SELECTIVE REDUCTION OF ALKYNES TO CIS-ALKENES BY HYDROMETALLATION USING [(PH3P)CUH]6

被引:73
作者
DAEUBLE, JF [1 ]
MCGETTIGAN, C [1 ]
STRYKER, JM [1 ]
机构
[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
关键词
D O I
10.1016/S0040-4039(00)97371-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Selective reduction of alkynes to the corresponding alkenes is reported using the stable, readily prepared copper(I) hydride reagent, [(Ph3P)CuH]6. Terminal alkynes are reduced at room temperature, unactivated internal alkynes react only at elevated temperature. Disubstituted alkynes with propargyl activation are also reduced, giving cis-olefins selectively. Protection of propargylic alcohol functionality is usually unnecessary, although fragmentation is sometimes competitive in sterically hindered cases. A tertiary propargyl acetate gave displacement to the allene exclusively. © 1990.
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页码:2397 / 2400
页数:4
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