Journal
TETRAHEDRON
Volume 70, Issue 27-28, Pages 4135-4146Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.03.080
Keywords
Benzocyclobutenone; Cycloaddition; Benzyne; Dehydrohalogenation; Benzocyclobutenol
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Funding
- UT Austin
- Cancer Prevention and Research Institute of Texas
- National Institute of General Medical Sciences [R01GM109054-01]
- Welch Foundation [F 1781]
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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-g 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. (C) 2014 Elsevier Ltd. All rights reserved.
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