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CuII-Catalyzed cis-Selective Synthesis of Ketoepoxides from Phenacyl Bromides and Water

Debasish Ghosh, Sabir A. Molla, Narendra Nath Ghosh, Saikat Khamarui* and Dilip K. Maiti*

*Government General Degree College, Kalna-1, Burdwan 713405; University of Calcutta, 92, A. P. C. Road, Kolkata 700009, India, Email: saikatkhamarui21gmail.com, dkmchemcaluniv.ac.in

D. Ghosh, S. A. Molla, N. N. Ghosh, S. Khamarui, D. K. Maiti, J. Org. Chem., 2023, 88, 9657-9667.

DOI: 10.1021/acs.joc.2c02835



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Abstract

A CuII-catalyzed oxidative C-C/O-C homocoupling/cyclization strategy of phenacyl bromides provides α,β-ketoepoxides with high yield and cis-selectivity. The homocoupling method was extended to cross-coupling between phenacyl bromides with benzyl bromides.

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proposed mechanism for homocoupling


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Key Words

C-O Coupling, C-C coupling


ID: J42-Y2023