PALLADIUM(0)-CATALYZED HYDROBORATION OF 1-BUTEN-3-YNES - PREPARATION OF ALLENYLBORANES

被引:81
作者
MATSUMOTO, Y
NAITO, M
HAYASHI, T
机构
[1] HOKKAIDO UNIV,CATALYSIS RES CTR,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN
[2] HOKKAIDO UNIV,GRAD SCH PHARMACEUT SCI,KITA KU,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1021/om00043a075
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reaction of 2-substituted 1-buten-3-ynes (CH2=CR-C=CH) with catecholborane in the presence of a palladium catalyst bearing a monodentate phosphine ligand such as PPh3 or PPh2(C6F5) proceeded in a 1,4-fashion to give (3-substituted 1,2-butadienyl)-1,3,2-benzodioxaboroles (CH3(R)C=C=CH(BO2C6H4)). Reaction of the allenylboranes with benzaldehyde gave the corresponding homopropargyl alcohols.
引用
收藏
页码:2732 / 2734
页数:3
相关论文
共 27 条
[1]   CATALYTIC ASYMMETRIC HYDROBORATION WITH OXAZABOROLIDINES [J].
BROWN, JM ;
LLOYDJONES, GC .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :869-872
[2]   SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITY IN CATALYZED AND UNCATALYZED HYDROBORATIONS OF ALLYLIC AMINE DERIVATIVES [J].
BURGESS, K ;
OHLMEYER, MJ .
TETRAHEDRON LETTERS, 1989, 30 (43) :5857-5860
[3]   DIASTEREOCONTROL IN RHODIUM-CATALYZED HYDROBORATION OF CHIRAL ACYCLIC ALLYLIC ALCOHOL DERIVATIVES [J].
BURGESS, K ;
OHLMEYER, MJ .
TETRAHEDRON LETTERS, 1989, 30 (04) :395-398
[4]   ENANTIOSELECTIVE HYDROBORATIONS CATALYZED BY RHODIUM(+1) COMPLEXES [J].
BURGESS, K ;
VANDERDONK, WA ;
OHLMEYER, MJ .
TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :613-621
[5]   SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES IN CATALYZED AND UNCATALYZED HYDROBORATIONS OF ACYCLIC ALLYLIC ALCOHOL DERIVATIVES - SECONDARY ORBITAL EFFECTS INVOLVING D-PI-P-PI INTERACTIONS [J].
BURGESS, K ;
CASSIDY, J ;
OHLMEYER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1020-1027
[6]   ENANTIOSELECTIVE HYDROBORATION MEDIATED BY HOMOCHIRAL RHODIUM CATALYSTS [J].
BURGESS, K ;
OHLMEYER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5178-5179
[7]   MANIPULATION OF SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES IN HYDROBORATIONS IN ACYCLIC ALLYLAMINE DERIVATIVES [J].
BURGESS, K ;
OHLMEYER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1027-1036
[8]   TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].
BURGESS, K ;
OHLMEYER, MJ .
CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191
[9]   ON DEUTERIUM-LABELING STUDIES FOR PROBING RHODIUM-CATALYZED HYDROBORATION REACTIONS [J].
BURGESS, K ;
VANDERDONK, WA ;
KOOK, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2949-2951
[10]   POLYHALOARYL COMPOUNDS CONTAINING PHOSPHORUS [J].
DUA, SS ;
EDMONDSO.RC ;
GILMAN, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1970, 24 (03) :703-&