N-Heterocyclic Carbene Mediated Activation of Tetravalent Silicon Compounds: A Critical Evaluation

被引:64
作者
Fuchter, Matthew J. [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
基金
美国国家科学基金会;
关键词
carbenes; Lewis bases; organocatalysis; polymers; silanes; GROUP-TRANSFER POLYMERIZATION; RING-OPENING POLYMERIZATION; CARBONYL-COMPOUNDS; TRANSESTERIFICATION REACTIONS; HYDROSILYLATION REACTIONS; CATALYTIC-ACTIVITY; LEWIS PAIR; COMPLEXES; ALDEHYDES; CYANOSILYLATION;
D O I
10.1002/chem.201001120
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An overview of the recent bibliography concerning the N-heterocyclic carbene (NHC)-mediated activation of tetravalent silicon compounds is presented. Diverse reactions are discussed, such as the NHC-mediated addition of silyl pronucleophiles to a variety of electrophiles, NHC-promoted organic and inorganic polymerisation and the reduction of CO2 by hydrosilanes as facilitated by NHCs. The review concludes with a discussion of the current knowledge regarding the role of Lewis acid-base NHC-Si interactions in the mechanistic course of these reactions.
引用
收藏
页码:12286 / 12294
页数:9
相关论文
共 69 条
[1]   STABLE CARBENES AS STRONG BASES [J].
ALDER, RW ;
ALLEN, PR ;
WILLIAMS, SJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (12) :1267-1268
[2]  
[Anonymous], 2008, ANGEW CHEM
[3]   THE INTERACTION OF ELECTROPHILIC SILANES (ME3SICLO4, ME3SII, ME3SICF3SO3, ME3SICL) WITH NUCLEOPHILES - THE NATURE OF SILYLATION MIXTURES IN SOLUTION [J].
BASSINDALE, AR ;
STOUT, T .
TETRAHEDRON LETTERS, 1985, 26 (28) :3403-3406
[4]  
Bonnette F., 2007, ANGEW CHEM, V119, P8786
[5]   Encapsulated N-heterocyclic carbenes in silicones without reactivity modification [J].
Bonnette, Fabien ;
Kato, Tsuyoshi ;
Destarac, Mathias ;
Mignani, Gerard ;
Cossio, Fernando P. ;
Baceiredo, Antoine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (45) :8632-8635
[6]  
Chase P.A., 2008, ANGEW CHEM, V120, P7543, DOI DOI 10.1002/ANGE.200802596
[7]   Hydrogen and amine activation by a frustrated Lewis pair of a bulky n-heterocyclic carbene and B(C6F5)3 [J].
Chase, Preston A. ;
Stephan, Douglas W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7433-7437
[8]   Percent buried volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry [J].
Clavier, Herve ;
Nolan, Steven P. .
CHEMICAL COMMUNICATIONS, 2010, 46 (06) :841-861
[9]  
Denmark S.E., 2008, ANGEW CHEM, V120, P1584
[10]   Lewis base catalysis in organic synthesis [J].
Denmark, Scott E. ;
Beutner, Gregory L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1560-1638