Allylcyanation of alkynes: Regio- and stereoselective access to functionalized di- or trisubstituted acrylonitriles

被引:118
作者
Nakao, Yoshiaki [1 ]
Yukawa, Tomoya [1 ]
Hirata, Yasuhiro [1 ]
Oda, Shinichi [1 ]
Satoh, Jun [1 ]
Hiyama, Tamejiro [1 ]
机构
[1] Kyoto Univ, Dept Chem Mat, Grad Sch Engn, Kyoto 6158510, Japan
关键词
D O I
10.1021/ja060519g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Allyl cyanides are found to add across alkynes in the presence of a nickel catalyst prepared from Ni(cod)2 and P(4-CF3-C6H4)3 in situ to give variously functionalized di- or trisubstituted acrylonitriles in highly stereoselective manners possibly via a π-allylnickel species as an intermediate. α-Siloxyallyl cyanides also react at the γ-position of a cyano group with both internal and terminal alkynes having various functional groups to give silyl enol ethers, which give the corresponding aldehydes or ketones upon hydrolysis. Copyright © 2006 American Chemical Society.
引用
收藏
页码:7116 / 7117
页数:2
相关论文
共 35 条
[31]   SIGMA-ARYL COMPOUNDS OF NICKEL, PALLADIUM, AND PLATINUM - SYNTHESIS AND BONDING STUDIES [J].
PARSHALL, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (08) :2360-2366
[32]   Alkynylation of benzonitriles via nickel catalyzed C-C bond activation [J].
Penney, JM ;
Miller, JA .
TETRAHEDRON LETTERS, 2004, 45 (25) :4989-4992
[33]   A mechanistic investigation of the carbon-carbon bond cleavage of aryl and alkyl cyanides using a cationic Rh(III) silyl complex [J].
Taw, FL ;
Mueller, AH ;
Bergman, RG ;
Brookhart, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9808-9813
[34]   Sterically demanding diphosphonite ligands -: Synthesis and application in nickel-catalyzed isomerization of 2-methyl-3-butenenitrile [J].
van der Vlugt, JI ;
Hewat, AC ;
Neto, S ;
Sablong, R ;
Mills, AM ;
Lutz, M ;
Spek, AL ;
Müller, C ;
Vogt, D .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (08) :993-1003
[35]   Nickel-catalyzed isomerization of 2-methyl-3-butenenitrile [J].
Wilting, J ;
Müller, C ;
Hewat, AC ;
Ellis, DD ;
Tooke, DM ;
Spek, AL ;
Vogt, D .
ORGANOMETALLICS, 2005, 24 (01) :13-15