SELECTIVE REDUCTION OF ALKYNES BY THE REAGENT SMI2 - TRANSITION-METAL CATALYSTS - PROTON DONORS

被引:16
作者
INANAGA, J [1 ]
YOKOYAMA, Y [1 ]
BABA, Y [1 ]
YAMAGUCHI, M [1 ]
机构
[1] KYUSHU UNIV 33,DEPT CHEM,FUKUOKA 812,JAPAN
关键词
D O I
10.1016/0040-4039(91)80083-I
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkynes were selectively reduced to cis-olefins under mild conditions by Sml2 in admixture with first-row transition metal catalysts and appropriate proton donors, in which the corresponding transition metal hydrides are presumed as the reactive species. The conditions also effected the conversion of 1,6-diynes to the corresponding five-membered carbocycles.
引用
收藏
页码:5559 / 5562
页数:4
相关论文
共 23 条
[1]   SELECTIVE REDUCTION OF ALKENES AND ALKYNES BY REAGENT LITHIUM ALUMINUM HYDRIDE TRANSITION-METAL HALIDE [J].
ASHBY, EC ;
LIN, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (13) :2567-2572
[2]   THE USE OF RIEKE ZINC METAL IN THE SELECTIVE REDUCTION OF ALKYNES [J].
CHOU, WN ;
CLARK, DL ;
WHITE, JB .
TETRAHEDRON LETTERS, 1991, 32 (03) :299-302
[3]  
COLLMAN JP, 1980, PRINCIPLES APPLICATI, P523
[4]   SELECTIVE REDUCTION OF ALKYNES TO CIS-ALKENES BY HYDROMETALLATION USING [(PH3P)CUH]6 [J].
DAEUBLE, JF ;
MCGETTIGAN, C ;
STRYKER, JM .
TETRAHEDRON LETTERS, 1990, 31 (17) :2397-2400
[5]  
ITO T, 1980, TETRAHEDRON LETT, V21, P1343
[6]   REDUCTION OF ACETYLENES TO (Z)-OLEFINS BY MEANS OF LOW-VALENT NIOBIUM OR TANTALUM [J].
KATAOKA, Y ;
TAKAI, K ;
OSHIMA, K ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1990, 31 (03) :365-368
[7]   METAL-PROMOTED CYCLIZATION .19. NOVEL BICYCLIZATION OF ENYNES AND DIYNES PROMOTED BY ZIRCONOCENE DERIVATIVES AND CONVERSION OF ZIRCONABICYCLES INTO BICYCLIC ENONES VIA CARBONYLATION [J].
NEGISHI, E ;
HOLMES, SJ ;
TOUR, JM ;
MILLER, JA ;
CEDERBAUM, FE ;
SWANSON, DR ;
TAKAHASHI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3336-3346
[8]   STEREOSELECTIVE CYCLIZATION OF ENYNES MEDIATED BY METALLOCENE REAGENTS [J].
RAJANBABU, TV ;
NUGENT, WA ;
TABER, DF ;
FAGAN, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (21) :7128-7135
[9]   SEMIHYDROGENATION OF ACETYLENES - MODIFIED LINDLAR CATALYST [J].
RAJARAM, J ;
NARULA, APS ;
CHAWLA, HPS ;
DEV, S .
TETRAHEDRON, 1983, 39 (13) :2315-2322
[10]   CP2TICL2-CATALYZED GRIGNARD EXCHANGE-REACTIONS WITH ACETYLENES - A CONVENIENT METHOD FOR PREPARATION OF E-ALKENYL GRIGNARD-REAGENTS [J].
SATO, F ;
ISHIKAWA, H ;
SATO, M .
TETRAHEDRON LETTERS, 1981, 22 (01) :85-88