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Pd-Catalyzed Isocyanide Assisted Reductive Cyclization of 1-(2-Hydroxyphenyl)-propargyl Alcohols for 2-Alkyl/Benzyl Benzofurans and Their Useful Oxidative Derivatization

Manda Rajesh, Nuligonda Thirupathi, Thota Jagadeshwar Reddy, Sanjeev Kanojiya and Maddi Sridhar Reddy*

*Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India, Email: msreddycdri.res.in

M. Rajesh, N. Thirupathi, T. J. Reddy, S. Kanojiya, M. S. Reddy, J. Org. Chem., 2015, 80, 12311-12320.

DOI: 10.1021/acs.joc.5b02204 (free Supporting Information)


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Abstract

An isocyanide-mediated and Pd-catalyzed 5-exo-dig reductive cyclization of 1-(2-hydroxyphenyl)-propargyl alcohols provides 2-alkyl/benzyl benzofurans in excellent yields. The reaction features a high substrate scope and is insensitive to air. Further, a direct metal-free C-H functionalization (azidation, alkoxylation, and hydroxylation) and selective oxidative cleavage of 2-benzylfurans are described.

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Key Words

benzofurans


ID: J42-Y2015