Metal vinylidenes and allenylidenes in catalysis: Applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis

被引:453
作者
Bruneau, C [1 ]
Dixneuf, PH [1 ]
机构
[1] Univ Rennes 1, Inst Chim, CNRS, UMR 6509, F-35042 Rennes, France
基金
加拿大自然科学与工程研究理事会;
关键词
alkene metathesis; allenylidenes; anti-Markovnikov addition; homogeneous catalysis; vinylidenes;
D O I
10.1002/anie.200501391
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The involvement of a catalytic metal vinylidene species was proposed for the first time in 1986 to explain the regioselective formation of vinyl carbamates directly from terminal alkynes, carbon dioxide, and amines. Since this initial report, various metal vinylidenes and allenylidenes, which are key activation intermediates, have proved extremely useful for many alkyne transformations. They have contributed to the rational design of new catalytic reactions. This 20th anniversary is a suitable occasion to present the advancement of organometallic vinylidenes and allenylidenes in catalysis. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2176 / 2203
页数:28
相关论文
共 303 条
[1]  
Abdallaoui IA, 2002, J MOL CATAL A-CHEM, V182, P577
[2]  
Ackermann L, 2001, SYNLETT, P397
[3]   Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM [J].
Ackermann, L ;
Fürstner, A ;
Weskamp, T ;
Kohl, FJ ;
Herrmann, WA .
TETRAHEDRON LETTERS, 1999, 40 (26) :4787-4790
[4]  
Akiyama R, 2002, ANGEW CHEM, V114, P2714
[5]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[6]   Formation of a cyclobutylidene ring: Intramolecular [2+2] cycloaddition of allyl and vinylidene C=C bonds under mild conditions [J].
Alvarez, P ;
Lastra, E ;
Gimeno, J ;
Bassetti, M ;
Falvello, LR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2386-2387
[7]   Hydration of terminal alkynes to aldehydes in aqueous micellar solutions by ruthenium(II) catalysis; first anti-Markovnikov addition of water to propargylic alcohols [J].
Alvarez, P ;
Bassetti, M ;
Gimeno, J ;
Mancini, G .
TETRAHEDRON LETTERS, 2001, 42 (48) :8467-8470
[8]  
[Anonymous], RUTHENIUM ORGANIC SY
[9]  
[Anonymous], J CHEM RES MINIPRINT
[10]  
[Anonymous], 1995, ANGEW CHEM, V107, P356