Concise Synthesis of Functionalized Benzocyclobutenones.

Concise Synthesis of Functionalized Benzocyclobutenones.
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DOI:
10.1016/j.tet.2014.03.080
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发表时间:
2014-07-08
期刊:
影响因子:
2.1
通讯作者:
Dong, Guangbin
Dong, Guangbin
中科院分区:
化学3区
文献类型:
--
作者:
Chen, P. -H.;Savage, Nikolas A.;Dong, Guangbin

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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.
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