Rhodium(I)-Catalyzed Decarbonylative Spirocyclization through C-C Bond Cleavage of Benzocyclobutenones: An Efficient Approach to Functionalized Spirocycles

被引：90

作者：

Xu, Tao ^{[1
]}

Savage, Nikolas A. ^{[1
]}

Dong, Guangbin ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 07期

关键词：

CC activation; decarbonylation; homogeneous catalysis; rhodium; spirocycles; CARBON-CARBON BOND; ACTIVATION; CATALYSIS; COMPLEXES; CARBOACYLATION; PALLADIUM(II); ELIMINATION; INSERTION; OLEFINS; SYSTEMS;

D O I：

10.1002/anie.201310149

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The rhodium-catalyzed formation of all-carbon spirocenters involves a decarbonylative coupling of trisubstituted cyclic olefins and benzocyclobutenones through CC activation. The metal-ligand combination [{Rh(CO)(2)Cl}(2)]/P(C6F5)(3) catalyzed this transformation most efficiently. A range of diverse spirocycles were synthesized in good to excellent yields and many sensitive functional groups were tolerated. A mechanistic study supports a hydrogen-transfer process that occurs through a -H elimination/decarbonylation pathway.

引用

页码：1891 / 1895

页数：5

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[1]

[Anonymous], 2009, Organotransition Metal Chemistry. From Bonding to Catalysis

[2] THE ORGANOMETALLIC CHEMISTRY OF ALKANES [J].