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A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel-Crafts Acylation of Vinyl Chlorides

Yingju Xu*, Mark McLaughlin*, Cheng-yi Chen, Robert A. Reamer, Peter G. Dormer and Ian W. Davies

*Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., Rahway, New Jersey 07065, Email: yingju_xumerck.com, mark_mclaughlinmerck.com

Y. Xu, M. McLaughlin, C.-y. Chen, R. A. Reamer, P. G. Dormer, I. W. Davies, J. Org. Chem., 2009, 74, 5100-5103.

DOI: 10.1021/jo900696k (free Supporting Information)


Abstract

An intramolecular Friedel-Crafts-type cyclization of vinyl chlorides and subsequent Pd-catalyzed cross-coupling reactions allow the synthesis of 3,5-diarylcyclopentenones. The requisite vinyl chloride-bearing arylacetic acid precursors are readily available by straightforward alkylation of arylacetic acid esters.

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Key Words

Friedel Crafts Acylation, Suzuki Coupling, Cyclopentenones


ID: J42-Y2009-2140