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化学进展 2019, Vol. 31 Issue (2/3): 351-367 DOI: 10.7536/PC180704 前一篇   后一篇

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糖基氮杂环卡宾及其过渡金属配合物的合成与催化性能

周中高**(), 元洋洋, 徐国海, 陈正旺, 李梅   

  1. 1. 赣南师范大学化学化工学院 赣州 341000
  • 收稿日期:2018-07-05 出版日期:2019-02-15 发布日期:2018-12-20
  • 通讯作者: 周中高
  • 基金资助:
    国家自然科学基金项目(21562002); 江西省高等学校功能材料化学重点实验室开发课题(FMC16201)
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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:2018-07-05 Online:2019-02-15 Published:2018-12-20
  • 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)

N-杂环卡宾(NHCs)及其金属配合物是有机金属化学学科的研究热点,在催化领域获得广泛应用。向NHCs杂环添加新颖官能团,构建复杂NHCs及其金属配合物可实现不同催化性能。糖类化合物具有生物相容性、水溶性、手性、无毒副作用且广泛存在于自然界,将糖取代基引入NHCs不仅可以改善水溶性,还可以引入手性元素。糖基-NHCs及其金属配合物在催化和药化领域显现出巨大潜力。本文就国内外含单糖D-吡喃葡萄糖、D-吡喃半乳糖、β-氨基葡萄糖、氨基半乳糖和氨基甘露糖等糖基衍生NHCs前体及NHCs金属配合物的重要研究成果进行了综述。根据糖基稠环碳原子与NHCs杂环的连接方式,将NHCs及其金属配合物分为5种类型,包括C-1、C-2、C-3、C-6及其他。从糖基-NHCs及其过渡金属配合物的合成、结构和催化性能方面进行了深入讨论,着重介绍了糖基和NHCs及其金属配合物在催化性能之间的关联性,并进行了简短的评述。最后,对糖基-NHCs及其过渡金属配合物的催化性能特别是在不对称反应中的应用前景及其影响因素进行了展望。

关键词： 糖类化合物, N-杂环卡宾, 过渡金属配合物, 水溶性, 催化性能

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
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图1 糖基-NHCs及其配合物的常见四大类连接模式
Fig. 1 Four types of linking modes of sugar based NHCs and their complexes
图2 糖基C-1连接NHCs-Ir配合物3的合成[32]
Fig. 2 Synthetic scheme of sugar C-1 type NHCs-Ir complex 3[32]
图3 糖基C-1连接NHCs-Pd配合物7和咪唑-2硫酮8[33]
Fig. 3 Synthetic scheme of sugar C-1 type NHCs-Pd 7 and imidazole-2 thione 8[33]
图4 咪唑盐催化Umpolung反应合成γ-丁内酯
Fig. 4 Synthesis of γ-butyrolactone by imidazolium salts catalyzed Umpolung reaction
图5 糖基C-1连接NHCs-Ru配合物12的合成[34]
Fig. 5 Synthetic scheme of sugar C-1 NHCs-Ru complexes 12[34]
图6 ROMP、RCM、CM和AROCM反应[34]
Fig. 6 ROMP, RCM, CM and AROCM reactions[34]
图7 糖基C-1连接NHCs-Pt配合物19的合成[35]
Fig. 7 Synthetic scheme of sugar C-1 NHCs-Pt complex 19[35]
图8 糖基C-1连接NHCs-Ni配合物21的合成[37]
Fig. 8 Synthetic scheme of sugar C-1 NHCs-Ni complex 21[37]
图9 糖基C-1连接NHCs-Rh、Ir配合物22和23的合成[38]
Fig. 9 Synthetic scheme of sugar C-1 type NHCs-Ru, Ir complexes 22 and 23[38]
图10 糖基C-1连接Ims 27~29的合成及其催化性能[39]
Fig. 10 Synthesis and catalytic activity of sugar C-1 Ims 27~29[39]
图11 糖基C-1连接咪唑盐 30的合成及其催化性能[41]
Fig. 11 Synthesis and catalytic activity of sugar C-1 type Ims 30[41]
图12 糖基C-1连接C-C-N型钯配合物33的合成及催化[42]
Fig. 12 Synthesis and catalytic activity of sugar C-1 C-C-N type Pd complexes 33[42]
图13 糖基C-1连接C—C—N型钯配合物36的合成及催化[43]
Fig. 13 Synthesis and catalytic activity of sugar C-1 C—C—N type Pd complexes 36[43]
图14 糖基C-1连接咪唑盐37的合成及催化[44]
Fig. 14 Synthesis and catalytic activity of sugar C-1 type imidazolium salt 37[44]
图15 糖基C-1连接咪唑盐39的合成[45]
Fig. 15 Synthesis of sugar C-1 type imidazolium salt 39[45]
图16 糖基C-1连接咪唑盐39的催化性能
Fig. 16 Catalytic activity of sugar C-1 type imidazolium salt 39
图17 NHCs-Ru、Ir配合物42~44的合成及催化[46]
Fig. 17 Synthesis and catalytic activity of NHCs-Ru, Ir complexes 42~44[46]
图18 糖基C-1连接钯配合物47、50~52的合成及催化[47]
Fig. 18 Synthesis and catalytic activity of sugar C-1 type Pd complexes 47, 50~52[47]
图19 糖基C-1连接双NHCs钯配合物54的合成及催化[48]
Fig. 19 Synthesis and catalytic activity of sugar C-1 type bis-NHCs Pd complexes 54[48]
图20 糖基C-1连接双NHCs前体55的合成及催化[49]
Fig. 20 Synthesis and catalytic activity of sugar C-1 type bis-NHCs precursors 55[49]
图21 糖基C-2连接NHCs-Rh配合物57和58的合成及催化[50]
Fig. 21 Synthesis and catalytic activity of sugar C-2 type NHCs-Rh 57 and 58[50]
图22 糖基C-3连接NHCs-Rh配合物63的合成[51]
Fig. 22 Synthesis of sugar C-3 type NHCs-Rh 63[51]
图23 糖基C-3连接NHCs-Pd配合物67的合成及催化[53]
Fig. 23 Synthesis and catalytic activity of sugar C-3 type NHCs-Pd 67[53]
图24 糖基C-3连接双咪唑啉盐70及NHCs-Pd、Au配合物71和72的合成[56,57]
Fig. 24 Synthesis of sugar C-3 type bis-Ims 70, NHCs-Pd, Au complexes 71 and 72[56,57]
图25 糖基C-6连接NHCs前体73的合成[58]
Fig. 25 Synthesis of sugar C-6 NHCs precursor 73[58]
图26 糖基C-6连接NHCs-Pd配合物76和77的合成[59]
Fig. 26 Synthesis of sugar C-6 NHCs-Pd complexes 76 and 77[59]
图27 糖基C-6连接NHCs-Pd配合物76和77的催化性能[59]
Fig. 27 Catalytic activity of sugar C-6 type NHCs-Pd complexes 76 and 77[59]
图28 其他方式连接糖基咪唑盐78~81的合成[61]
Fig. 28 Synthesis of other type sugar based Ims 78~81[61]
图29 其他方式连接糖基咪唑盐84和85的合成[62]
Fig. 29 Synthesis of other type sugar based Ims 84 and 85[62]
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