Progress in Chemistry

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A Special Issue to Commemorate Huang Zhi-Tangs 90th Birth Anniversary

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Preface

Progress in Chemistry. 2018, 30(5): 1-2.

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. Preface[J]. Progress in Chemistry, 2018, 30(5): 1-2.
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Prof. Huang Zhi-Tang——A Biographic Overview

Progress in Chemistry. 2018, 30(5): 3-6.

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. Prof. Huang Zhi-Tang——A Biographic Overview[J]. Progress in Chemistry, 2018, 30(5): 3-6.

Review

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Macrocyclic and Supramolecular Chemistry: From Heteracalixaromatics to Coronarenes——In Memory of Professor Zhi-Tang Huang

Xiang Wang*

Progress in Chemistry. 2018, 30(5): 463-475. https://doi.org/10.7536/PC180219

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Xiang Wang*. Macrocyclic and Supramolecular Chemistry: From Heteracalixaromatics to Coronarenes——In Memory of Professor Zhi-Tang Huang[J]. Progress in Chemistry, 2018, 30(5): 463-475.

Research history of heteracalixaromatics and coronarenes are introduced herein. The design and synthesis of heteracalixaromatics and coronarenes are summarized followed by the description of the macrocyclic conformation and cavity structures. Molecular recognition towards cations, anions and neutral guest species and property of molecular assembly of these macrocyclic hosts are presented. Applications of heteracalixaromatics and coronarenes in the fabrication of functional materials are also demonstrated briefly. The future perspectives of heteracalixaromatics and coronarenes in macrocyclic and supramolecular chemistry are discussed at last.
Contents
1 Introduction
2 Macrocyclic and supramolecular chemistry of heteracalixaromatics
2.1 Synthesis and functionalization of heteracalixaromatics and their structures
2.2 Molecular recognition and molecular assembly of heteracalixaromatics
2.3 Probing high valent organocopper chemistry using heteracalixaromatics as molecular tools
2.4 Miscellaneous applications of heteracalixaromatics
3 Macrocyclic and supramolecular chemistry of coronarenes
3.1 Synthesis and functionalization reactions of coronarenes
3.2 Structure of coronarenes
3.3 Property and application of coronarenes
4 Conclusion and outlook
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Asymmetric Supramolecular Catalysis Based on Macrocyclic Host Molecules

Yuping Tang, Yanmei He, Yu Feng, Qinghua Fan

Progress in Chemistry. 2018, 30(5): 476-490. https://doi.org/10.7536/PC180137

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Yuping Tang, Yanmei He, Yu Feng, Qinghua Fan. Asymmetric Supramolecular Catalysis Based on Macrocyclic Host Molecules[J]. Progress in Chemistry, 2018, 30(5): 476-490.

In recent years, supramolecular catalysis has become one of the most challenging research frontiers and hot spots in organic synthesis based on the continuous combination and fusion of supramolecular chemistry and catalysis, and has achieved gratifying development. As the main objectives in supramolecular chemistry, macrocyclic host molecules have gained much attention in supramolecular catalysis due to their reversible recognition and self-assembly with different guest molecules and thus can realize pre-organization of reactants within the catalytic cavities. In the last 20 years, progress has been achieved in supramolecular catalysis based on macrocyclic host molecules. This review will focus on the recent progress in asymmetric supramolecular catalysis based on the representative macrocyclic host molecules, such as crown ethers, cyclodextrins, calixarenes, and their counterparts. The design and synthesis of chiral catalysts, the use of these catalysts in enantioselective reactions, especially, the supramolecular modulation of catalytic activity and selectivity via host-guest association will be introduced. Meanwhile, the limitation and drawbacks of current study and the perspectives for its future development will also be discussed.
Contents
1 Introduction
2 Asymmetric catalysis based on crown ethers and their counterparts
2.1 Chiral crown ether-based metal catalysts
2.2 Chiral metallacrown ether catalysts
2.3 Chiral pseudorotaxane and rotaxane catalysts
2.4 Podands in asymmetric catalysis
3 Asymmetric catalysis based on cyclodextrins
3.1 Cyclodextrin as macroreactor
3.2 Cyclodextrin-based metal catalysts
3.3 Cyclodextrin organocatalysts
4 Asymmetric catalysis based on chiral calixarenes
4.1 Chiral calixarene-based metal catalysts
4.2 Chiral calixarene-based organocatalysts
4.3 Inherently chiral calixarene catalysts
5 Conclusion and outlook
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Recent Advance in Catalytic Asymmetric Friedel-Crafts Reactions

Yu Zhang, Xiaohua Liu, Lili Lin, Xiaoming Feng*

Progress in Chemistry. 2018, 30(5): 491-504. https://doi.org/10.7536/PC171121

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Yu Zhang, Xiaohua Liu, Lili Lin, Xiaoming Feng*. Recent Advance in Catalytic Asymmetric Friedel-Crafts Reactions[J]. Progress in Chemistry, 2018, 30(5): 491-504.

Catalytic asymmetric Friedel-Crafts reaction is one of the most efficient methods for the construction of optically active aryl-or heteroaryl-containing compounds. Since Friedel and Crafts reported the first example in 1877, this reaction has attracted wide attention. In recent twenty years, asymmetric catalytic Friedel-Crafts reaction has been well studied in the presence of a number of chiral bifunctional organocatalysts (such as derivatives of cinchona alkaloids, chiral prolinol ethers, chiral phosphoric acids, chiral thiourea, etc.) and various metal and chiral ligand (chiral N,N'-dioxide, chiral bis(oxazoline), chiral Schiff base) complexes. In this paper, we summarize the recent progress in asymmetric Friedel-Crafts reactions of phenols, pyrroles, furans and thiophenes. Finally, the deficiencies as well as the perspective of the Friedel-Crafts reaction have been highlighted.
Contents
1 Introduction
2 Catalytic asymmetric Friedel-Crafts reactions of phenols
2.1 Imines as the electrophiles
2.2 1, 2-Diketones as the electrophiles
2.3 Nitroalkenes as the electrophiles
2.4 α, β-Unsaturated carbonyl compounds as the electrophiles
2.5 Others double bonds as the electrophiles
3 Catalytic asymmetric Friedel-Crafts reactions of pyrroles
3.1 Nitroalkenes as the electrophiles
3.2 α, β-Unsaturated carbonyl compounds as the electrophiles
3.3 Others
4 Catalytic asymmetric Friedel-Crafts reactions of furans and thiophenes
5 Conclusion
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Asymmetric Organo/Palladium Combined Catalysis

Zhiyong Han, Liuzhu Gong*

Progress in Chemistry. 2018, 30(5): 505-512. https://doi.org/10.7536/PC171206

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Zhiyong Han, Liuzhu Gong*. Asymmetric Organo/Palladium Combined Catalysis[J]. Progress in Chemistry, 2018, 30(5): 505-512.

Organo/metal combined catalysis integrates the catalytic activity of the organocatalyst and metal complex to enable the creation of unprecedented protocols by simultaneous or sequential activation of chemical bonds. On the basis of the activation modes and catalytic pathways, the combined catalysis could be divided into cooperative catalysis, relay catalysis and sequential catalysis. In recent years, the metal/organo combined catalysis has received a great deal of attention, leading to many unprecedented protocols thanks to increasingly deep insight into the concepts of organocatalysis and transition-metal catalysis. Palladium complexes have been one of the most important types of transition metal catalysts and have widely been applied to the organic synthesis. This review will be focused on highlighting recent progress in asymmetric combined catalysis of chiral organocatalysts and palladium complexes, including chiral amines, Brønsted acids, and nucleophilic Lewis bases combined with palladium complexes for the creation of unprecedented transformations. The key issues that need to be addressed in this field are discussed and the perspective of the emerging area are also described.
Contents
1 Introduction
2 Chiral amine/palladium combined catalysis
3 Chiral Brønsted acid/palladium combined catalysis
4 Chiral nucleophilic Lewis base/palladium combined catalysis
5 Conclusion
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Me₃Si(TMS) Chemistry: Transition-Metal Catalyzed Activation and Utilization of C(sp³)-Si Bond

Qi Yang, Kunbing Ouyang, Liang Liu, Zhenfeng Xi

Progress in Chemistry. 2018, 30(5): 513-527. https://doi.org/10.7536/PC171237

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Qi Yang, Kunbing Ouyang, Liang Liu, Zhenfeng Xi. Me₃Si(TMS) Chemistry: Transition-Metal Catalyzed Activation and Utilization of C(sp³)-Si Bond[J]. Progress in Chemistry, 2018, 30(5): 513-527.

The C(sp³)-Si bond in trialkylsilyl groups such as SiMe₃ is among the most frequently encountered C-Si bonds, because many compounds are substituted with trialkylsilyl groups. Silacycles, particularly siloles, have been recognized and extensively studied for their potential applications in organic synthetic chemistry, material science, and medicinal chemistry. The cleavage and applications of the bond is important in organic synthetic chemistry. However, classic methods require a stoichiometric amount of either organo-magnesium or organolithium reagent. The harsh conditions in these methods do not tolerate many functional groups, thus limiting the synthetic application of these approaches. Transition-metal-catalyzed cleavage of the C(sp³)-Si bonds would be ideal for overcoming the limitation. The process not only shows a new and unique entry to functionalize the C(sp³)-Si bond, but also presents a powerful method to synthesize diverse organosilanes. Up to now, the majority of successful examples, in which the strategy of transition metal catalyzed reactions was applied into activation of C(sp³)-Si bonds, has concentrated on the strained cyclic compounds and functionalized substrates. Hence, the activation of unactivated C(sp³)-Si bonds remains a challenging issue. This review article summarizes recent reports on transition-metal-catalyzed cleavage and synthetic applications of the C(sp³)-Si bonds. In addition, the organometallic reagent-promoted cleavage of C(sp³)-Si bonds is also presented for comparison.Contents
1 Introduction
2 Organometallic reagent-promoted cleavage of C(sp³)—Si bonds
3 Transition-metal-catalyzed cleavage and synthetic applications of C(sp³)—Si bonds
3.1 Organosilicon compounds containing strong electron-withdrawing groups
3.2 Strained silacycles
3.3 Inactive C(sp³)—Si bonds
4 Conclusion
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SmI₂ and Titanocene-Mediated Coupling Reactions of α-Aminoalkyl Radicals and Applications to the Synthesis of Aza-Heterocycles

Xiao Zheng, Pei-Qiang Huang*

Progress in Chemistry. 2018, 30(5): 528-546. https://doi.org/10.7536/PC171249

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Xiao Zheng, Pei-Qiang Huang*. SmI₂ and Titanocene-Mediated Coupling Reactions of α-Aminoalkyl Radicals and Applications to the Synthesis of Aza-Heterocycles[J]. Progress in Chemistry, 2018, 30(5): 528-546.

Carbon-carbon formation at N-α-carbon is an essential transformation in the synthesis of nitrogen-containing compounds. N-α-Carbocations (iminium ions), N-α-carbanions, and N-α-aminoalkyl radicals constitute three major classes of intermediates for this goal. The carbon-carbon forming reactions based on N-α-aminoalkyl radicals is advantageous over other two classes of intermediates for being able to run the reactions under mild neutral conditions. Moreover, because N-α-aminoalkyl radicals are umpolung of N-α-carbocations (iminium ions), the approaches based on these intermediates are complementary. In this regard, Kagan reagent (samarium diiodide, SmI₂), a mild single-electron reductant, has emerged as a versatile reagent for the generation and coupling of N-α-aminoalkyl radicals. In this review, recent progresses on the carbon-carbon forming reactions at N-α-carbon via Kagan reagent is summarized. A number of nitrogen-containing substrates including imines, nitrones, hemiaminals, imides and amides have been shown to be valuable precursors to generate α-aminoalkyl radicals. The in situ coupling reactions of the latter with aldehydes/ketones, or electron-deficient alkenes lead to the formation of N-α-C—C bonds. These methods allow flexible access to diverse N-α-C functionalized compounds. To overcome some limitations of Kagan reagent, methods based on the titanocene-catalyzed generation of N-α-aminoalkyl radicals have also been developed. Many of these methods have been applied to the concise syntheses of medicinal-relevant compounds, alkaloids or key intermediates.
Contents
1 Introduction
2 SmI₂-mediated radical coupling of imines
3 SmI₂-mediated radical coupling of nitrones
3.1 Methodology research
3.2 Synthetic application
4 SmI₂-mediated radical coupling of chiral N-tert-butanesulfinyl imines
4.1 Methodology research
4.2 Synthetic application
5 SmI₂-mediated radical coupling of hemiaminal
5.1 Methodology research
5.2 Synthetic application
6 SmI₂-mediated radical coupling of imides, amides and nitriles
6.1 Radical coupling of imides
6.2 Radical coupling of amides
6.3 Radical coupling of nitriles
7 An extension research:titanocene-catalyzed radical coupling reactions
8 Conclusion and outlook
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CO₂: C₁ Synthon in Carboxylation Reactions

Yu Zhang, Jinghe Cen, Wenfang Xiong, Chaorong Qi, Huanfeng Jiang*

Progress in Chemistry. 2018, 30(5): 547-563. https://doi.org/10.7536/PC171251

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Yu Zhang, Jinghe Cen, Wenfang Xiong, Chaorong Qi, Huanfeng Jiang*. CO₂: C₁ Synthon in Carboxylation Reactions[J]. Progress in Chemistry, 2018, 30(5): 547-563.

Recently organic synthesis using carbon dioxide as the raw material has attracted considerable attention from scientists because of the resourceful and environmental factors. Especially, transition metal-catalyzed carboxylation reaction is an efficient method to construct carboxylic acids and their derivatives, which is regarded as one of ideal strategies for carbon dioxide utilization and carbon recycle. The recent advances of carboxylation reaction of CO₂ with various substrates (electrophiles, hydrocarbons, nucleophiles) are reviewed herein.
Contents
1 Introduction
2 Carboxylation of CO₂ with various electrophiles
2.1 Carboxylation of CO₂ with halogenated hydrocarbon
2.2 Carboxylation of CO₂ with esters or alcohols
2.3 Carboxylation of CO₂ with other electrophiles
3 Carboxylation of CO₂ with diverse hydrocarbon compounds containing C—H bond
3.1 Carboxylation of CO₂ with hydrocarbon containing C(sp)—H bond
3.2 Carboxylation of CO₂ with hydrocarbon containing C(sp²)—H bond
3.3 Carboxylation of CO₂ with hydrocarbon containing C(sp³)—H bond
4 Carboxylation of CO₂ with different nucleophiles
4.1 Carboxylation of CO₂ with organoboranes
4.2 Carboxylation of CO₂ with organosilanes
5 Conclusion and outlook
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C—C and C-Heteroatom Bonds Formation Based on Oxidative Dehydrogenation of Cyclohexanones

Jinjin Chen, Dan Chang, Fuhong Xiao, Guojun Deng*

Progress in Chemistry. 2018, 30(5): 564-577. https://doi.org/10.7536/PC171132

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Jinjin Chen, Dan Chang, Fuhong Xiao, Guojun Deng*. C—C and C-Heteroatom Bonds Formation Based on Oxidative Dehydrogenation of Cyclohexanones[J]. Progress in Chemistry, 2018, 30(5): 564-577.

Cyclohexanones are cheap and commercially available compounds and widely used as raw materials and key intermediates in organic synthesis. Dehydrogenative aromatization has emerged as an efficient approach to access functionalized arenes. The transformation commonly involves sequential nucleophilic addition, dehydration and catalytically oxidative dehydrogenation. Compared to the traditional arylation methods, this strategy avoids the use of harsh reaction conditions and the production of halide wastes. In addition, the chemo-and regioselectivities can be easily controlled. Therefore, this method offers a milder/greener means for the synthesis of functionalized arenes. This review mainly focuses on the direct formation of C—C and C-heteroatom bonds using cyclohexanones as raw materials and the extension of these methodologies to the construction of various heterocycles.
Contents
1 Introduction
2 Oxidative dehydrogenation of cyclohexanones
3 C—C bond formation based on cyclohexanones
4 C-heteroatom bond formation based on cyclohexanones
4.1 C—O bond formation
4.2 C—S bond formation
4.3 C—N bond formation
4.4 Construction of heterocycles based on the formation of C-heteroatom bond
5 Conclusion and outlook
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Total Synthesis of the Akuammiline Alkaloid Strictamine

Xiaoyu Liu, Tao Xiao, Yong Qin

Progress in Chemistry. 2018, 30(5): 578-585. https://doi.org/10.7536/PC171131

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Xiaoyu Liu, Tao Xiao, Yong Qin. Total Synthesis of the Akuammiline Alkaloid Strictamine[J]. Progress in Chemistry, 2018, 30(5): 578-585.

Due to their complex and diverse structures and significant bioactivities, the chemical synthesis of the akuammiline alkaloids has been highly pursued in the chemical community. Strictamine, as one of the representative members in this natural product family, is structurally featured by a cage like methanoquinolizidine framework and an all-carbon quaternary stereogenic center at C7, posing a great challenge in synthesis. Pursuit in the total synthesis of strictamine has a history of over four decades; however, the breakthroughs came until the recent two years. This review briefly summarizes the three total syntheses and four formal syntheses of strictamine that have been reported since 2016, by highlighting the key strategies and reactions employed in each of the synthesis. Moreover, perspectives in this research field have also been suggested at the end of this review.
Contents
1 Introduction
2 Total synthesis and formal total synthesis of strictamine
2.1 Asymmetric total synthesis of (+)-strictamine by the Garg group
2.2 Total synthesis of (±)-strictamine by the Zhu group
2.3 Total synthesis of (±)-strictamine by the Zu group
2.4 Formal synthesis of (±)-strictamine by the Fujii/Ohno group
2.5 Formal synthesis of (+)-strictamine by the Snyder group
2.6 Formal synthesis of (±)-strictamine by the Gaich group
2.7 Formal synthesis of (+)-strictamine by the Qin group
3 Conclusion and outlook
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Synthesis and Glycosidase Inhibitory Activities of Fluorinated Iminosugars

Yixian Li, Yuemei Jia, Chuyi Yu

Progress in Chemistry. 2018, 30(5): 586-600. https://doi.org/10.7536/PC171248

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Yixian Li, Yuemei Jia, Chuyi Yu. Synthesis and Glycosidase Inhibitory Activities of Fluorinated Iminosugars[J]. Progress in Chemistry, 2018, 30(5): 586-600.

Iminosugars have shown great potential in pharmaceutical industry due to their potent glycosidase inhibition, anti-virus and anti-cancer activities. Systematic study of structure-activity relationship of iminosugars will help to develop highly active and selective lead compounds. Fluorination is usually the most used method of studying structure-activity relationship. This review summarized the reported synthetic strategies of fluorinated iminosugars and the related glycosidase inhibitory activities. The synthetic strategies are roughly categorized to three types, namely, fluorine containing building blocks, fluorinated sugars and fluorinating reagents, and each of them is reviewed with merits, disadvantages and its application. The structure-activity relationship of some representative iminosugars is then preliminarily concluded based on the reported glycosidase inhibitory activities of fluorinated iminosugars. Intact iminosugar ring is believed important for interaction with enzymes, while fluorination of side chain and the fused ring would influence inhibitory spectrum and potency, respectively. Therefore, the current research results of fluorinated iminosugars have made important contributions to iminosugar chemistry. With fluorine as tool, the structure-activity relationship of iminosugars can be further completed and corrected in the future, and therefore would certainly help to provide profound foundation for the design and syntheses of iminosugars with potential medicinal values, and thus effectively promote the related drug discovery.
Contents
1 Iminosugar and its application
2 Synthetic strategies of fluorinated iminosugars and related biological activity study
2.1 Synthesis of fluorinated iminosugars from fluorinated building blocks
2.2 Synthesis of fluorinated iminosugars from fluorinated sugars
2.3 Synthesis of fluorinated iminosugars by subsequent introduction of fluorine
3 Fluorination in structure-activity relationship study of iminosugars
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Chiral Calixarenes and Their Supramolecular Chirality

Jun Luo, YanSong Zheng

Progress in Chemistry. 2018, 30(5): 601-615. https://doi.org/10.7536/PC171134

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Jun Luo, YanSong Zheng. Chiral Calixarenes and Their Supramolecular Chirality[J]. Progress in Chemistry, 2018, 30(5): 601-615.

Calixarenes are concave molecules consisting of phenol units and linking methylenes. Due to facile modification and controllable conformations, calixarenes are regarded as the third generation of host molecules. At molecular level, chiral calixarenes can be classified into calixarenes with chiral subunits, inherently chiral calixarenes, and bridging chiral calixarenes, according to the structural feature of the chirality elements. At supramolecular level, calixarenes can self-assemble or assemble with other molecules or ions into nanoscale aggregates of diverse topologies in solution, solid state, and two-dimensional surface, through non-covalent bonds. The study on chiral calixarenes and their supramolecular chirality not only has theoretical significance in chiral structures, origin of chirality, and so on, but also shows great potential in chiral sensors, chiral catalysts, chiral separation materials, chiral vehicles, and chiral nano-materials etc. This review focuses on the progress in the design, synthesis, structure, and function of representative calixarenes with molecular chirality and supramolecular chirality in the last decade. Emphasis is laid on the advantages of calixarene skeletons in forming novel molecular chirality and supramolecular chirality as well as in realizing specific and novel functions. It is expected that more exceptional chiral calixarene molecules and chiral calixarene supramolecular materials will be obtained as advancement of synthetic technology and supramolecular designs in calixarene studies.
Contents
1 Introduction
2 Calixarenes with chiral subunits
2.1 As solvating reagents
2.2 As gelators
2.3 As asymmetric catalysts
3 Inherently chiral calixarenes
3.1 Upper rim/Lower rim-substituted
3.2 Meta-substituted
3.3 Calixarenes containing chiral methylene bridge carbon
4 Calixarene supramolecular chirality
4.1 Supramolecular chirality driven by acid-base reaction
4.2 Supramolecular chirality driven by electrostatic attraction
4.3 Supramolecular chirality driven by hydrogen bonding
4.4 Supramolecular chirality driven by coordination
4.5 Supramolecular chirality driven by van der Waals interaction
4.6 Supramolecular chirality driven by π-π interaction
4.7 Supramolecular chirality driven by inclusion
5 Conclusion and outlook
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The Directional Threading of Guests and Construction of Orientational Assemblies Based on Three-Dimensional Nonsymmetrical Hosts

Hanxiao Wang, Ying Han, Chuanfeng Chen*

Progress in Chemistry. 2018, 30(5): 616-627. https://doi.org/10.7536/PC171201

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Hanxiao Wang, Ying Han, Chuanfeng Chen*. The Directional Threading of Guests and Construction of Orientational Assemblies Based on Three-Dimensional Nonsymmetrical Hosts[J]. Progress in Chemistry, 2018, 30(5): 616-627.

In host-guest chemistry, taking precise control over the isomerism in the complexation process can not only simplify and regulate the structures of the final assemblies including mechanical interlocked molecules, but also exert great influence on their performance in carrying out tasks as molecular machines. When a linearly nonsymmetrical guest threads into the cavity of a three-dimensionally nonsymmetrical host, orientational isomers will be formed in theory resulting from the nondegenerate threading directions of the guest. This type of isomerism has been attracting the interest of researchers, and much progress has been made in how to control the threading direction of the guest by rationally designing the structures of both the host and the guest. In this review, the characterization methods of the relative host-guest orientation, the mechanism of the threading process and the construction of assemblies based on the complexation between three-dimensionally nonsymmetrical hosts, including cyclodextrins, calixarenes and triptycene-derived macrocycles, and linearly nonsymmetrical guests are summarized. The prospect and future application are also discussed.
Contents
1 Introduction
2 The general strategies of determining the threading direction and its selectivity of the guest molecule
2.1 The strategies of determining the relative orientation of host and guest
2.2 The strategies of determining the relative amount of orientational isomers
3 Directional threading of guests and construction of assemblies based on cyclodextrins
3.1 Thermodynamically controlled directional threading
3.2 Kinetically controlled directional threading
4 Directional threading of guests and construction of assemblies based on calixarenes
4.1 Directional threading based on urea-derived calix[6]arenes
4.2 Directional threading based on classical calix[6]arenes
5 Directional threading and construction of assemblies based on triptycene-derived macrocyclic hosts
6 Conclusion and outlook
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Design and Synthesis of Conjugated Aromatic Macrocyclic Rings That Can Serve as Carbon Nanotube Segments

Qi-Feng Zhou, Bo Jiang*, Hai-Bo Yang*

Progress in Chemistry. 2018, 30(5): 628-638. https://doi.org/10.7536/PC170909

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Qi-Feng Zhou, Bo Jiang*, Hai-Bo Yang*. Design and Synthesis of Conjugated Aromatic Macrocyclic Rings That Can Serve as Carbon Nanotube Segments[J]. Progress in Chemistry, 2018, 30(5): 628-638.

Design and synthesis of conjugated aromatic macrocyclic rings that are directly linked by C—C bonds has been currently attracting wide interests because these aromatic macrocyclic rings can be used for synthesis of single-walled carbon nanotubes through the "bottom-up" stratety. Conventional methods of preparing carbon nanotubes, such as arc method, chemical vapor deposition method and so on, are difficult to form the uniform single-walled carbon nanotubes. This "bottom-up" synthetic strategy provides a feasible method for the highly efficient synthesis of highly homogeneous single-walled carbon nanotubes. For this reason, the "bottom-up" synthetic strategy has become an on-going hot spot for the synthesis of single-walled carbon nanotubes, although it is still a big challenge. This article summarizes new progress in the design and synthesis of two-dimensional (2D) carbon nanorings, 2D carbon nanobelts and three-dimensional (3D) carbon nanocages. In particular, this article focuses on the design principle and synthesis methods of 2D carbon nanorings and highlights the polycyclic aromatic hydrocarbon (PAHs) carbon nanorings. Polycyclic aromatic hydrocarbons usually have excellent photoelectric properties. Thus, the conjugated carbon nanohoops constructed by these PAHs moieties may exhibit new photoelectric properties.
Contents
1 Introduction
2 2D conjugated carbon nanoring
2.1 Cycloparaphenylenes
2.2 Carbon nanoring of polycyclic aromatic hydrocarbons
3 2D conjugated carbon nanobelts
4 3D conjugated carbon nanocages
5 Properties and applications
6 Conclusion
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Heterocyclic Ketene Aminals: Leading Molecules to Construct Molecular Diversity Fused Heterocyclic Compounds

Lingbin Kong, Shengjiao Yan*, Jun Lin*

Progress in Chemistry. 2018, 30(5): 639-657. https://doi.org/10.7536/PC171208

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Lingbin Kong, Shengjiao Yan*, Jun Lin*. Heterocyclic Ketene Aminals: Leading Molecules to Construct Molecular Diversity Fused Heterocyclic Compounds[J]. Progress in Chemistry, 2018, 30(5): 639-657.

Heterocyclic ketene aminals (HKAs) are a class of fascinating and versatile synthetic building blocks for use in the construction of a wide range of molecular diversity fused heterocyclic compounds and synthetic drugs. With the further development of HKAs, great progress has been made in reactions of HKAs as a binucleophilic reagents with a variety of electrophilic substrates. Based on the structural characteristics and reaction performances of HKAs, construction of a variety of potentially bioactive natural-like polycyclic heterocyclic compounds with HKAs and 1,1-enediamine as synthons is reviewed herein.
Contents
1 Introduction
2 Construction of natural-like polycyclic fused heterocyclic compounds with pyrrole as the core skeleton of the molecule
2.1 Construction of multi-substituted bicyclic pyrrole derivatives
2.2 Construction of polycyclic pyrrole derivatives
3 Construction of polycyclic fused heterocyclic compounds with pyridine as the core skeleton of the molecule.
3.1 Construction of bicyclopyridine derivatives
3.2 Construction of polycyclic pyridine derivatives
4 Construction of polycyclic fused heterocyclic compounds with indole as the core skeleton of the molecule
5 Construction of polycyclic fused heterocyclic compounds with quinoline as the core skeleton of the molecule
6 Construction of natural polycyclic fused heterocyclic compounds with bridge and spiro analogues as the core skeleton of the molecule
7 Construction of other types of polycyclic fused ring heterocyclic compounds
8 Conclusion and outlook
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Application of Organic Conjugated Frameworks Containing Seven-Membered Carbon Rings in Optoelectronic Materials

Dandan Shi, Xisha Zhang, Deqing Zhang

Progress in Chemistry. 2018, 30(5): 658-672. https://doi.org/10.7536/PC171220

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Dandan Shi, Xisha Zhang, Deqing Zhang. Application of Organic Conjugated Frameworks Containing Seven-Membered Carbon Rings in Optoelectronic Materials[J]. Progress in Chemistry, 2018, 30(5): 658-672.

Benzene is one of the most widely used units in organic opto-electronic materials. Different from six-membered benzene, seven-membered carbon conjugated system has seen much less applications in opto-electronic materials. Until recently, some attention has been paid to this field. Because of its different molecular orbital characteristic from benzene and easiness to be oxidized, seven-membered carbon ring conjugated system may introduce special and interesting properties to organic opto-electronic materials. In this paper, the conjugated seven-membered carbon rings are reviewed from the point of discovery, synthesis and structural investigation. Then, the skeleton types containing seven-membered carbon rings are analyzed and the synthetic methods for these skeleton types are demonstrated. The applications of conjugated molecules containing seven-membered carbon rings in near infrared absorptive materials, organic field effect transistors, organic solar cells and stimuli-responsive systems are introduced. In the end, the future developments of this field are discussed.
Contents
1 Introduction
2 Conjugated frameworks containing 7-membered carbon ring
3 Representative synthetic methods for conjugated molecules containing 7-membered carbon ring
3.1 Cyclo-addition and electro-cyclization reactions
3.2 Friedel-Crafts reaction
3.3 Condensation reaction
3.4 Scholl-type oxidative coupling reaction
3.5 Metal mediated alkene or alkyne cyclization
3.6 Functionalization of 7-membered ring
4 Application of conjugated molecules containing 7-membered carbon ring in near infrared absorption systems
5 Application of conjugated molecules containing 7-membered carbon ring in organic field effect transistors
5.1 Azulene based systems
5.2 Non-azulene based systems
6 Application of conjugated molecules containing 7-membered carbon ring in organic solar cells
7 Application of conjugated molecules containing 7-membered carbon ring in stimuli-responsive systems
7.1 Azulene based systems
7.2 Non-azulene based systems
8 Conclusion and outlook
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Construction and Functions of Supramolecular Cyclodextrin Gels

Qian Zhao, Shenghua Li, Yu Liu*

Progress in Chemistry. 2018, 30(5): 673-683. https://doi.org/10.7536/PC180101

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Qian Zhao, Shenghua Li, Yu Liu*. Construction and Functions of Supramolecular Cyclodextrin Gels[J]. Progress in Chemistry, 2018, 30(5): 673-683.

Cyclodextrin, as a good water-soluble and biocompatible macrocycle, has attracted much attention due to its specific bonding with inorganic/organic/biological substrates. While combining the advantages of solid's elasticity and liquid's mobility, the gels are widely applied in many fields. The supramolecular gels based on cyclodextrin stand out in the field of soft materials due to the integration of the advantages of cyclodextrin and gel, Therefore, this review embarking upon the construction of cyclodextrin gels, discusses the driving force of their formation such as hydrogen bonding, host-guest bonding and ion interaction. Then the latest research on the functions of supramolecular cyclodextrin gels including biological/sensing/adsorption/smart materials including sliding materials are reviewed, which provide an outlook for the construction and functions of new cyclodextrin gels. Finally, the development and application of cyclodextrin gel materials are discussed and prospected.
Contents
1 Introduction
2 Construction of cyclodextrin supramolecular gels
2.1 Hydrogen bonding
2.2 Host-guest complexation
2.3 Ionic interaction
3 Application of cyclodextrin supramolecular gels
3.1 Biological applications
3.2 Sensors
3.3 Removal of pollutants in water environment
3.4 Smart materials
4 Conclusion
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Polyimide Foams for High Temperature Applications

Yunhan Xu, Leilei Wang, Aijun Hu, Lili Yuan, Zhiyuan Wang, Shiyong Yang*

Progress in Chemistry. 2018, 30(5): 684-691. https://doi.org/10.7536/PC180220

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Yunhan Xu, Leilei Wang, Aijun Hu, Lili Yuan, Zhiyuan Wang, Shiyong Yang*. Polyimide Foams for High Temperature Applications[J]. Progress in Chemistry, 2018, 30(5): 684-691.

Polyimide foams, due to the outstanding combined properties including low dielectric and thermal insulating, acoustic absorbing, high strength-to-weight ratio, cost effectiveness, etc., have been extensively used in many high-tech fields such as the aerospace, aviation, ship, energy and environmental protection, etc., in recent years. There are two types of polyimide foams, the soft one having opened-cell in structures and the rigid one having closed-cell in structures. Polyimide foams are usually produced by thermal foaming of the polyimide precursor, the molecular weight-controlled poly(amic ester) resins, which are prepared by polycondensation of aromatic dianhydride and aromatic diamines. There are obvious effects of chemical structure of the molecular weight-controlled polyimide precursor resins on mechanical and thermal properties of the polyimide foams. The molecular weights of the polyimide precursor resins also have apparent impacts on the foam densities, mechanical and thermal properties. In this paper, the progress of polyimide foams, especially the chemical structures, properties and applications, will be described.
Contents
1 Introduction
2 Soft and opened-cell polyimide foams
2.1 Development
2.2 Typical properties of soft and opened-cell polyimide foams
2.3 Applications of soft and opened-cell polyimide foams
3 Rigid and closed-cell polyimide foams
3.1 Preparation methods
3.2 Relationship of heat treatment temperature of precursor resin and foam structure
3.3 Relationship of main chain structure of resin and foam properties
4 Conclusion
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Biosynthetic Mechanisms of Alkaloids from Actinomycetes

Tingting Huang, Zihua Zhou, Qi Liu, Xiaozheng Wang, Wenli Guo, Shuangjun Lin*

Progress in Chemistry. 2018, 30(5): 692-702. https://doi.org/10.7536/PC180324

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Tingting Huang, Zihua Zhou, Qi Liu, Xiaozheng Wang, Wenli Guo, Shuangjun Lin*. Biosynthetic Mechanisms of Alkaloids from Actinomycetes[J]. Progress in Chemistry, 2018, 30(5): 692-702.

Alkaloid natural products generally have complex and diverse chemical structures and exhibit a wide range of biological activities, and therefore are of great interest to biologists, chemists, and pharmacists. Apart from plants, microorganisms have been identified as the most important source of natural alkaloids. Microorganisms, especially actinomycetes, produce many secondary metabolites including alkaloids. Studies on the biosynthesis of skeletons and pharmacophores of alkaloids produced by actinomycetes not only enrich our understanding of the biosynthetic mechanism of natural products, but also provide important genetic elements in order to generate these compounds or the derivatives by designed and man-made synthetic pathways in heterologous host using synthetic biology. This review provides a summary of recent research advances in elucidating the biosynthesis of alkaloids from actinomycetes. The detailed biochemical mechanisms have been summarized in modular biosynthetic machineries and non-modular enzymatic systems, respectively.
Contents
1 Introduction
2 Modular biosynthesis of alkaloids
2.1 Diketopiperazine alkaloids
2.2 Pyrrolobenzodiazepines
2.3 Tetrahydroisoquinolines
2.4 Maremycins family
3 Non-modular biosynthesis of alkaloids
3.1 Streptonigrinoids
3.2 Spirocycloproprane family
3.3 Indolocarbazole alkaloids
3.4 Aminobenzoquinone-aziridine alkaloids
4 Conclusion and outlook

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