The Resurgence of the Highly Ylidic N-Heterocyclic Olefins as a New Class of Organocatalysts

被引:109
作者
Crocker, Reece D. [1 ]
Nguyen, Thanh V. [1 ]
机构
[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia
基金
澳大利亚研究理事会;
关键词
BrOnsted; Lewis bases; amines; olefins; organocatalysis; ylides; FRUSTRATED LEWIS PAIRS; POLYMERIZATION; COORDINATION; ALANE; CO2; CARBODICARBENES; PRECURSORS; COMPLEXES; CARBENES; ADDUCTS;
D O I
10.1002/chem.201503575
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In recent decades, N-heterocyclic carbenes have become established as a prevalent family of organocatalysts. N-Heterocyclic olefins, the alkylidene derivatives of N-heterocyclic carbenes, have recently also emerged as efficient promoters for CO2 fixation and polymerization reactions. Their extraordinarily strong Lewis/BrOnsted basicity suggests great potential as a new class of organocatalysts for a broad range of reactions in synthetic chemistry.
引用
收藏
页码:2208 / 2213
页数:6
相关论文
共 47 条
[1]   Intercepting low oxidation state main group hydrides with a nucleophilic N-heterocyclic olefin [J].
Al-Rafia, S. M. Ibrahim ;
Malcolm, Adam C. ;
Liew, Sean K. ;
Ferguson, Michael J. ;
McDonald, Robert ;
Rivard, Eric .
CHEMICAL COMMUNICATIONS, 2011, 47 (24) :6987-6989
[2]  
[Anonymous], 2012, ANGEW CHEM-GER EDIT
[3]  
[Anonymous], 2010, ANGEW CHEM
[4]  
Denmark S.E., 2008, ANGEW CHEM, V120, P1584
[5]   Lewis base catalysis in organic synthesis [J].
Denmark, Scott E. ;
Beutner, Gregory L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1560-1638
[6]   Reversible carboxylation of N-heterocyclic carbenes [J].
Duong, HA ;
Tekavec, TN ;
Arif, AM ;
Louie, J .
CHEMICAL COMMUNICATIONS, 2004, (01) :112-113
[7]   Sustainable conversion of carbon dioxide: the advent of organocatalysis [J].
Fiorani, Giulia ;
Guo, Wusheng ;
Kleij, Arjan W. .
GREEN CHEMISTRY, 2015, 17 (03) :1375-1389
[8]   Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes [J].
Flanigan, Darrin M. ;
Romanov-Michailidis, Fedor ;
White, Nicholas A. ;
Rovis, Tomislav .
CHEMICAL REVIEWS, 2015, 115 (17) :9307-9387
[9]   Carbodicarbenes-divalent carbon(0) compounds exhibiting carbon-carbon donor-acceptor bonds [J].
Frenking, Gernot ;
Tonner, Ralf .
WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE, 2011, 1 (06) :869-878
[10]   Coordination chemistry of ene-1,1-diamines and a prototype "Carbodicarbene" [J].
Fuerstner, Alois ;
Alcarazo, Manuel ;
Goddard, Richard ;
Lehmann, Christian W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (17) :3210-3214