Palladium-catalyzed ring-opening cyclization/hydrosilylation of 1-cyclopropyl-1,6-heptadienes to form (E)-1-butenyl cyclopentanes

被引：17

作者：

Wang, X ^{[1
]}

Stankovich, SZ ^{[1
]}

Widenhoefer, RA ^{[1
]}

机构：

[1] Duke Univ, Paul M Gross Chem Lab, Durham, NC 27708 USA

来源：

ORGANOMETALLICS | 2002年 / 21卷 / 05期

关键词：

D O I：

10.1021/om010907l

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of 4,4-dicarbomethoxy-1-cyclopropyl-1,6-heptadiene (3) and HSiMe(2)OSiPh(2)t-Bu catalyzed by a 1:1 mixture of (phen)Pd(Me)Cl (2) (phen = 1,10-phenanthroline) and NaBAr4 [Ar = 3,5-C6H3(CF3)(2)] in CH2Cl2 at 0 degreesC for 12 h formed (E)-trans-3-(1-butenyl)-4-(3-tert-butyl-1,1-dimethyl-3,3-diphenyldisiloxymethyl)-1,1-dicarbomethoxycyclopentane (4) in 93% isolated yield as a 25:1 mixture of isomers. Reaction of 4,4-dicarbomethoxy-1-cyclobutyl-1,6-heptadiene (122) and HSiMe(2)OSiPh(2)t-Bu (0.13 M) catalyzed by 2/NaBAr4 formed a 1.9:1 mixture of 1-pentenyl- (132) and cyclobutylmethyl- (142) cyclopentanes in 73% combined yield.

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页码：901 / 905

页数：5

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