Tandem Catalytic Triple-Bond Cleavage of Alkyne in Association with Aldehyde, Alkene, and Water

被引：11
作者：
Cha, Kyung-Mi
Jo, Eun-Ae
Jun, Chul-Ho [1 ]
机构：
[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
来源：
SYNLETT | 2009年 / 18期
关键词：
C-C triple-bond cleavage; C-H bond activation; rhodium; homogeneous catalysis; C-H BOND; INTERMOLECULAR HYDROACYLATION; ORGANIC-SYNTHESIS; ACTIVATION; COMPLEX; FUNCTIONALIZATION; OLEFINS; RH(I); TRANSIMINATION; EFFICIENT;
D O I：
10.1055/s-0029-1218000
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this tandem reaction the carbon-carbon triple bond of an alkyne is catalytically cleaved in association with aldehyde, alkene, and H2O under catalyst mixtures of Rh(l), 2-amino-3-plicoline, primary amine, and acid. The reaction starts with chelation-assisted hydroacylation of the alkyne with an aldehyde. The retro-Mannich-type fragmentation of the resulting alpha,beta-unsaturated ketimine by an amine and acid affords a ketimine and an aldimine, which is trapped by an alkene and give ketones after hydrolysis.
引用
收藏
页码：2939 / 2942
页数：4
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