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Sequential and One-Pot Reactions of Phenols with Bromoalkynes for the Synthesis of (Z)-2-Bromovinyl Phenyl Ethers and Benzo[b]furans

Shihua Wang, Pinhua Li, Lin Yu and Lei Wang*

*Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China, Email:

S. Wang, P. Li, L. Yu, L. Wang, Org. Lett., 2011, 13, 5968-5971.

DOI: 10.1021/ol202383z (free Supporting Information)


Benzo[b]furans were prepared in one pot based on the addition/palladium-catalyzed C-H bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers exclusively. Subsequent intramolecular cyclization affords 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C-H bond functionalizations.

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ID: J54-Y2011-3270