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Concise Synthesis of Functionalized Benzocyclobutenones.

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 can be run on a 10-gram scale with an increased yield. A number of functional groups including alkenes and alkynes are tolerated. Coupling of benzynes with ketene silyl acetals to give 8-substituted benzocyclobutenones is also demonstrated.

SUBMITTER: Chen PH

PROVIDER: S-EPMC4049219 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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Concise Synthesis of Functionalized Benzocyclobutenones.

Chen Peng-Hao PH Savage Nikolas A NA Dong Guangbin G

Tetrahedron 20140701 27-28

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 <i>n</i>-BuLi and THF, followed by oxidation of the benzocyclobutenol intermediates to provide benzocyclobutenones. The [2+2] reaction can be run on a 10-gram scale with an increased yield. A number of functional group ...[more]

PMID: 24926108

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