Nickel-promoted alkylative or arylative carboxylation of alkynes

被引:107
作者
Takimoto, M [1 ]
Shimizu, K [1 ]
Mori, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
D O I
10.1021/ol016585z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Nickel-promoted alkylative or arylative carboxylation of terminal alkynes via a carbon dioxide fixation process was investigated. In the presence of a stoichiometric amount of a zero-valent nickel complex, the reaction of alkynes with CO2 gave a nickelacycle, which was reacted with various organozinc reagents under very mild conditions to provide beta,beta'-disubstituted, alpha,beta -unsaturated carboxylic acids in a highly regio- and stereoselective manner.
引用
收藏
页码:3345 / 3347
页数:3
相关论文
共 23 条
[1]   CARBON-DIOXIDE AS AN ALTERNATIVE C1 SYNTHETIC UNIT - ACTIVATION BY TRANSITION-METAL COMPLEXES [J].
BEHR, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (05) :661-678
[2]   GENERAL-APPROACH TO HIGHLY FUNCTIONALIZED BENZYLIC ORGANOMETALLICS OF ZINC AND COPPER [J].
BERK, SC ;
KNOCHEL, P ;
YEH, MCP .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5789-5791
[3]   REACTIONS OF CARBON-DIOXIDE WITH CARBON CARBON BOND FORMATION CATALYZED BY TRANSITION-METAL COMPLEXES [J].
BRAUNSTEIN, P ;
MATT, D ;
NOBEL, D .
CHEMICAL REVIEWS, 1988, 88 (05) :747-764
[4]   OXANICKELACYCLOPENTENE DERIVATIVES FROM NICKEL(0), CARBON-DIOXIDE, AND ALKYNES [J].
BURKHART, G ;
HOBERG, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (01) :76-76
[5]  
CURE J, 1969, B SOC CHIM FR, P2471
[6]  
CURE J, 1968, B SOC CHIM FR, P3244
[7]   ELECTROGENERATED NICKEL(0) CATALYZED CARBON-DIOXIDE INCORPORATION INTO ALPHA,OMEGA-DIYNES [J].
DERIEN, S ;
DUNACH, E ;
PERICHON, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 385 (03) :C43-C46
[8]   FROM STOICHIOMETRY TO CATALYSIS - ELECTROREDUCTIVE COUPLING OF ALKYNES AND CARBON-DIOXIDE WITH NICKEL BIPYRIDINE COMPLEXES - MAGNESIUM-IONS AS THE KEY FOR CATALYSIS [J].
DERIEN, S ;
DUNACH, E ;
PERICHON, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8447-8454
[9]   ELECTROCHEMICAL CARBOXYLATION OF TERMINAL ALKYNES CATALYZED BY NICKEL-COMPLEXES - UNUSUAL REGIOSELECTIVITY [J].
DUNACH, E ;
PERICHON, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 352 (1-2) :239-246
[10]   The organometallic chemistry of carbon dioxide [J].
Gibson, DH .
CHEMICAL REVIEWS, 1996, 96 (06) :2063-2095