REGIOSPECIFIC AND STEREOSPECIFIC PREPARATION OF BETA-(ALKYLTHIO)ALKENYL-1,3,2-BENZODIOXABOROLES BY NICKEL-CATALYZED HYDROBORATION OF THIOACETYLENES WITH CATECHOLBORANE

被引：87

作者：

GRIDNEV, ID ^{[1
]}

MIYAURA, N ^{[1
]}

SUZUKI, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC ENGN,DEPT APPL CHEM,SAPPORO,HOKKAIDO 060,JAPAN

来源：

ORGANOMETALLICS | 1993年 / 12卷 / 02期

关键词：

D O I：

10.1021/om00026a053

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Hydroboration of 1-(alkylthio)-1-alkynes with catecholborane 1 in the presence of 3 mol % of NiCL2-(dppe) or NiCl2(dppp) proceeds regio- and stereospecifically, giving excellent yields of [(E)-1-(alkylthio)-1-alken-2-yl]-1,3,2-benzodioxaboroles 2 under mild conditions.

引用

页码：589 / 592

页数：4

共 35 条

[1] ASYMMETRIC CATALYSIS - MECHANISM OF ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROSILATION
BERGENS, SH
NOHEDA, P
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2128 - 2135
[2] Brandsma L., 1971, PREPARATIVE ACETYLEN
[3] CATECHOLBORANE (1,3,2-BENZODIOXABOROLE) AS A NEW, GENERAL MONOHYDROBORATION REAGENT FOR ALKYNES - CONVENIENT SYNTHESIS OF ALKENEBORONIC ESTERS AND ACIDS FROM ALKYNES VIA HYDROBORATION
BROWN, HC
GUPTA, SK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) : 4370 - &
[4] HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE
BROWN, HC
GUPTA, SK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) : 5249 - 5255
[5] HYDROBORATION .65. RELATIVE REACTIVITIES OF REPRESENTATIVE ALKENES AND ALKYNES TOWARD HYDROBORATION BY CATECHOLBORANE
BROWN, HC
CHANDRASEKHARAN, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) : 5080 - 5082
[6] BROWN HC, 1975, ORGANIC SYNTHESES VI
[7] BUBNOV YN, 1971, ZH OBSCH KIM, P131
[8] SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES IN CATALYZED AND UNCATALYZED HYDROBORATIONS OF ACYCLIC ALLYLIC ALCOHOL DERIVATIVES - SECONDARY ORBITAL EFFECTS INVOLVING D-PI-P-PI INTERACTIONS
BURGESS, K
CASSIDY, J
OHLMEYER, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) : 1020 - 1027
[9] ENANTIOSELECTIVE HYDROBORATION MEDIATED BY HOMOCHIRAL RHODIUM CATALYSTS
BURGESS, K
OHLMEYER, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) : 5178 - 5179
[10] TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS
BURGESS, K
OHLMEYER, MJ
[J]. CHEMICAL REVIEWS, 1991, 91 (06) : 1179 - 1191

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