Metal vinylidenes as catalytic species in organic reactions

被引:177
作者
Trost, Barry M. [1 ]
McClory, Andrew [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
atom economy; catalysis; chemoselectivity; organic synthesis; vinylidene ligands;
D O I
10.1002/asia.200700247
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Organic vinylidene species have found limited use in organic synthesis owing to their inaccessibility. In contrast, metal vinylidenes are much more stable and may be readily accessed through transition-metal activation of terminal alkynes. These electrophilic species may be trapped by a number of nucleophiles. Additionally, metal vinylidenes can participate in pericyclic reactions and processes that involve migration of a metal ligand to the vinylidene species. This Focus Review addresses the reactions and applications of metal vinylidenes in organic synthesis.
引用
收藏
页码:164 / 194
页数:31
相关论文
共 159 条
[11]   Transition metal complexes containing allenylidene, cumulenylidene, and related ligands [J].
Bruce, MI .
CHEMICAL REVIEWS, 1998, 98 (08) :2797-2858
[12]  
BRUCE MI, 1983, ADV ORGANOMET CHEM, V22, P59
[13]   CATALYTIC INCORPORATION OF CO-2 INTO ORGANIC SUBSTRATES - SYNTHESIS OF UNSATURATED CARBAMATES, CARBONATES AND UREAS [J].
BRUNEAU, C ;
DIXNEUF, PH .
JOURNAL OF MOLECULAR CATALYSIS, 1992, 74 (1-3) :97-107
[14]   Metal vinylidenes and allenylidenes in catalysis: Applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis [J].
Bruneau, C ;
Dixneuf, PH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) :2176-2203
[15]   Selective transformations of alkynes with ruthenium catalysts [J].
Bruneau, C ;
Dixneuf, PH .
CHEMICAL COMMUNICATIONS, 1997, (06) :507-512
[16]   ACETYLENE IN CATALYSIS - A ONE-STEP SYNTHESIS OF VINYLCARBAMATES WITH [RUCL2(NORBORNADIENE)]N [J].
BRUNEAU, C ;
DIXNEUF, PH ;
LECOLIER, S .
JOURNAL OF MOLECULAR CATALYSIS, 1988, 44 (02) :175-178
[17]   Metal vinylidenes in catalysis [J].
Bruneau, C ;
Dixneuf, PH .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (04) :311-323
[18]  
Bruneau C., 2006, ANGEW CHEM, V118, P2232
[19]   Ruthenium-promoted Z-selective head-to-head dimerization of terminal alkynes in organic and aqueous media [J].
Chen, XG ;
Xue, P ;
Sung, HHY ;
Williams, ID ;
Peruzzini, M ;
Bianchini, C ;
Jia, GC .
ORGANOMETALLICS, 2005, 24 (18) :4330-4332
[20]   RETRACTED: Rhodium-catalyzed arylative and alkenylative cyclization of 1,5-enynes induced by geminal carbometalation of alkynes (Retracted Article) [J].
Chen, Yiyun ;
Lee, Chulbom .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15598-15599