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Progress in Chemistry 2019, Vol. 31 Issue (2/3): 351-367 DOI: 10.7536/PC180704 Previous Articles   Next Articles

The Synthesis and Catalytic Activity of Sugar-Based NHCs and Their Transition Metal Complexes

Zhonggao Zhou**(), Yangyang Yuan, Guohai Xu, Zhengwang Chen, Mei Li   

  1. 1. College of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou 341000, China
  • Received: Online: Published:
  • Contact: Zhonggao Zhou
  • About author:
    ** E-mail:
  • Supported by:
    National Natural Science Foundation of China(21562002); Key Laboratory of Jiangxi University for Functional Materials Chemistry(FMC16201)
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N-Heterocyclic carbenes(NHCs) and their stable transition metal complexes rank among the most popular subjects for research in organometallic chemistry that have been widely used in the field of catalysis. Researchers are investigating NHCs metal complexes with increasingly complex NHCs components, adding new functional substituents to the NHCs heterocyclic ring. Sugar compounds are extremely abundant molecules and well known for their biocompatibility, water solubility, chirality and nontoxicity. It is not surprising that sugar substituents have been introduced into NHCs(sugar-based NHCs) to increase water solubility and chirality. Sugar-based NHCs and their metal complexes show great potential in the fields of catalysis and pharmacology. To understand the success of sugar-based NHCs, this review first presents the important research progress in sugar-based NHCs precursors and NHCs metal complexes containing monosaccharides such as D-glucopyranose, D-galactopyranose, β-glucosamine, galactosamine, and aminomannose are discussed. Overview, sugar-based NHCs and their metal complexes are divided into five categories according to the carbon-linked of sugar with fused ring(including C-1, C-2, C-3, C-6, and others). Then the main synthetic methods, handling, structure, and catalytic activity of sugar-based NHCs and their metal complexes are discussed in detail, roles of the sugar moiety, NHCs ligand and transition metal complexes related to these properties are highlighted. Finally, the catalytic activity, especially in asymmetric catalytic reaction, and the development trend of sugar-based NHCs precursors and NHCs transition metal complexes are prospected.

Key words: sugar, N-heterocyclic carbene, transition metal complex, water-soluble, catalytic activity
Fig. 1 Four types of linking modes of sugar based NHCs and their complexes
Fig. 2 Synthetic scheme of sugar C-1 type NHCs-Ir complex 3[32]
Fig. 3 Synthetic scheme of sugar C-1 type NHCs-Pd 7 and imidazole-2 thione 8[33]
Fig. 4 Synthesis of γ-butyrolactone by imidazolium salts catalyzed Umpolung reaction
Fig. 5 Synthetic scheme of sugar C-1 NHCs-Ru complexes 12[34]
Fig. 6 ROMP, RCM, CM and AROCM reactions[34]
Fig. 7 Synthetic scheme of sugar C-1 NHCs-Pt complex 19[35]
Fig. 8 Synthetic scheme of sugar C-1 NHCs-Ni complex 21[37]
Fig. 9 Synthetic scheme of sugar C-1 type NHCs-Ru, Ir complexes 22 and 23[38]
Fig. 10 Synthesis and catalytic activity of sugar C-1 Ims 27~29[39]
Fig. 11 Synthesis and catalytic activity of sugar C-1 type Ims 30[41]
Fig. 12 Synthesis and catalytic activity of sugar C-1 C-C-N type Pd complexes 33[42]
Fig. 13 Synthesis and catalytic activity of sugar C-1 C—C—N type Pd complexes 36[43]
Fig. 14 Synthesis and catalytic activity of sugar C-1 type imidazolium salt 37[44]
Fig. 15 Synthesis of sugar C-1 type imidazolium salt 39[45]
Fig. 16 Catalytic activity of sugar C-1 type imidazolium salt 39
Fig. 17 Synthesis and catalytic activity of NHCs-Ru, Ir complexes 42~44[46]
Fig. 18 Synthesis and catalytic activity of sugar C-1 type Pd complexes 47, 50~52[47]
Fig. 19 Synthesis and catalytic activity of sugar C-1 type bis-NHCs Pd complexes 54[48]
Fig. 20 Synthesis and catalytic activity of sugar C-1 type bis-NHCs precursors 55[49]
Fig. 21 Synthesis and catalytic activity of sugar C-2 type NHCs-Rh 57 and 58[50]
Fig. 22 Synthesis of sugar C-3 type NHCs-Rh 63[51]
Fig. 23 Synthesis and catalytic activity of sugar C-3 type NHCs-Pd 67[53]
Fig. 24 Synthesis of sugar C-3 type bis-Ims 70, NHCs-Pd, Au complexes 71 and 72[56,57]
Fig. 25 Synthesis of sugar C-6 NHCs precursor 73[58]
Fig. 26 Synthesis of sugar C-6 NHCs-Pd complexes 76 and 77[59]
Fig. 27 Catalytic activity of sugar C-6 type NHCs-Pd complexes 76 and 77[59]
Fig. 28 Synthesis of other type sugar based Ims 78~81[61]
Fig. 29 Synthesis of other type sugar based Ims 84 and 85[62]
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