Synthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols

Mohammad Rehan, Rajender Nallagonda, Braja Gopal Das, Tannu Meena and Prasanta Ghorai*

*Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal-462066, India, Email: pghoraiiiserb.ac.in

M. Rehan, R. Nallagonda, B. G. Das, T. Meena, P. Ghorai, J. Org. Chem., 2017, 82, 3411-3424.

DOI: 10.1021/acs.joc.6b02752

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Abstract

A regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cinnamyl phenols using [PdCl₂(CH₃CN)₂] as catalyst and benzoquinone as an oxidant provides functionalized 2-benzyl benzo[b]furans. Further, a one-pot, sequential synthesis of ortho-cinnamyl phenols, starting from readily available alcohols and phenols, followed by Pd-catalyzed oxidative annulation, has also been developed.

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Key Words

benzofurans, BQ

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ID: J42-Y2017