ORGANOLITHIUM REAGENTS BY REDUCTIVE DECYANATION OF NITRILES WITH LITHIUM AND A CATALYTIC AMOUNT OF 4,4'-DI-TERT-BUTYL-BIPHENYL IN A BARBIER-TYPE REACTION

被引:41
作者
GUIJARRO, D [1 ]
YUS, M [1 ]
机构
[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALICANTE,SPAIN
关键词
D O I
10.1016/S0040-4020(01)87024-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of different nitriles 1 with an excess of lithium powder (1:14 molar ratio) and a catalytic amount of 4,4'-di-tert-butylbiphenyl (5 mol %) in the presence of a carbonyl compound (Barbier-type conditions) in THF at low temperature (-30 or -78 degrees C) leads to the corresponding compounds 2 resulting from the coupling between the electrophile and the organolithium intermediate arising from a reductive decyanation of the starting nitrile 1. This new reaction can be also applied to the use of trimethylchlorosilane as electrophile at 0 degrees C.
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页码:3447 / 3452
页数:6
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