Cobalt-catalyzed alkyne-nitrile cyclotrimerization to form pyridines in aqueous solution

被引:73
作者
Fatland, AW [1 ]
Eaton, BE [1 ]
机构
[1] Washington State Univ, Dept Chem, Pullman, WA 99164 USA
关键词
D O I
10.1021/ol006327m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new, water-soluble cobalt(I) catalyst has been used in the aqueous, chemospecific, cyclotrimerization of one nitrile with two alkynes for the synthesis of highly functionalized pyridines. Several different functional groups are well incorporated in this transformation, including unprotected alcohols, ketones, and amines. Double isotopic crossover data, as well as nitrile dependence on the rate of product formation, suggest associative rate-determining coordination of the nitrile.
引用
收藏
页码:3131 / 3133
页数:3
相关论文
共 26 条
[1]  
Abel E.W., 1995, COMPREHENSIVE ORGANO
[2]   COBALT-CATALYZED PYRIDINE SYNTHESES FROM ALKYNES AND NITRILES [J].
BONNEMANN, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (07) :505-515
[3]  
BONNEMANN H, 1984, ASPECTS HOMOGENEOUS
[4]   ON THE ORIGIN OF PRODUCT SELECTIVITY IN AQUEOUS DIELS-ALDER REACTIONS [J].
BRESLOW, R ;
MAITRA, U .
TETRAHEDRON LETTERS, 1984, 25 (12) :1239-1240
[5]   Organometallic reactions in aqueous media. The nature of the organotin intermediate in the tin-mediated allylation of carbonyl compounds [J].
Chan, TH ;
Yang, Y ;
Li, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4452-4455
[6]   Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate [J].
Chan, TH ;
Yang, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3228-3229
[7]   Organometallic reactions in aqueous media. Allylation of aldehydes with diallylmercury or allylmercury bromide [J].
Chan, TH ;
Yang, Y .
TETRAHEDRON LETTERS, 1999, 40 (20) :3863-3866
[8]  
Collman J.P., 1987, PRINCIPLES APPL ORGA
[9]   Favoring alkene insertion over beta-hydride elimination: Aqueous media and ligands enable a double Heck reaction on a substrate for which beta-hydride elimination is possible [J].
Grotjahn, DB ;
Zhang, XW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 116 (1-2) :99-107
[10]  
GROTJAHN DB, 1993, SYNTHESIS-STUTTGART, P579