糖基氮杂环卡宾及其过渡金属配合物的合成与催化性能
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摘要
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。
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 newfunctional 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 showgreat potential in the fields of catalysis and pharmacology. To understand the success of sugar-based NHCs,this reviewfirst presents the important research progress in sugarbased NHCs precursors and NHCs metal complexes containing monosaccharides such as D-glucopyranose,Dgalactopyranose, 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.
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 newfunctional 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 showgreat potential in the fields of catalysis and pharmacology. To understand the success of sugar-based NHCs,this reviewfirst presents the important research progress in sugarbased NHCs precursors and NHCs metal complexes containing monosaccharides such as D-glucopyranose,Dgalactopyranose, 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.
引文
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[2] Wang W,Cui L,Sun P,Shi L,Yue C,Li F. Chem. Rev.,2018,118:9843.
[3] Engel S,Fritz E C,Ravoo B J. Chem. Soc. Rev.,2017,46:2057.
[4] Zhukhovitskiy A V,Mac Leod M J,Johnson J A. Chem. Rev.,2015,115:11503.
[5] Wang G,Ruhling A,Amirjalayer S,Knor M,Ernst J B,Richter C,Gao H J,Timmer A,Gao H Y,Doltsinis N L,Glorius F,Fuchs H. Nat. Chem.,2017,9:152.
[6] Crudden C M,Horton J H,Narouz M R,Li Z,Smith C A,Munro K, Baddeley C J, Larrea C R, Drevniok B,Thanabalasingam B,Mc Lean A B,Zenkina O V,Ebralidze I I,She Z,Kraatz H B,Mosey N J,Saunders L N,Yagi A. Nat.Commun.,2016,7:12654.
[7] Fung S K,Zou T,Cao B,Chen T,To W P,Yang C,Lok C N,Che C M. Nat. Commun.,2016,7:10655.
[8] Crudden C M,Horton J H,Ebralidze I I,Zenkina O V,Mclean A B,Drevniok B,She Z,Kraatz H B,Mosey N J,Seki T. Nat.Chem.,2014,6:409.
[9] Zhong R,Lindhorst A C,Groche F J,Kühn F E. Chem. Rev.,2017,117:1970.
[10] Benhamou L,Chardon E,Lavigne G,Bellemin-Laponnaz S,César V. Chem. Rev.,2011,111:2705.
[11] Grabulosa A,Granell J,Muller G. Coord. Chem. Rev.,2007,251:25.
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[13] Khramov D M,Lynch V M,Bielawski C W. Organometallics,2007,26:6042.
[14] Marion N,Díez-González S,Nolan S P. Angew. Chem. Int. Ed.,2007,46:2988.
[15] Fevre M,Pinaud J,Gnanou Y,Vignolle J,Taton D. Chem. Soc.Rev.,2013,42:2142.
[16] Díez-González S,Marion N,Nolan S P. Chem. Rev.,2009,109:3612.
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[52]周中高(Zhou Z G).福建师范大学硕士论文(Master’s Dissetation of Fujian Normal University),2009.
[53]张德志(Zhang D Z).福建师范大学硕士论文(Master’s Dissetation of Fujian Normal University),2009.
[54] Yao H,Zhang Y,Sun H,Shen Q. Eur. J. Inorg. Chem.,2009,2009:1920.
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[61] Huang J Y,Lei M,Wang Y G. Tetrahedron Lett.,2006,47:3047.
[62] Salman A A,Tabandeh M,Heidelberg T,Hussen R S D,Ali H M. Carbohydr. Res.,2015,412:28.
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