Tetrahedron

Concise synthesis of functionalized benzocyclobutenones

PH Chen, NA Savage, G Dong

Index: Chen; Savage, Nikolas A.; Dong, Guangbin Tetrahedron, 2014 , vol. 70, # 27-28 p. 4135 - 4146

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Citation Number: 5

Abstract

Abstract A concise approach to access functionalized benzocyclobutenones from 3- halophenol derivatives is described. This modified synthesis employs a [2+ 2] cycloaddition between benzynes generated from dehydrohalogenation of aryl halides using LiTMP and acetaldehyde enolate generated from n-BuLi and THF, followed by oxidation of the benzocyclobutenol intermediates to provide benzocyclobutenones. The [2+ 2] reaction ...