Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

Trevor C. Sherwood*, Hai-Yun Xiao*, Roshan G. Bhaskar, Eric M. Simmons, Serge Zaretsky, Martin P. Rauch, Robert R. Knowles, T. G. Murali Dhar

*Research and Development, Bristol-Myers Squibb Company, P.O. Box 4000, Princeton, New Jersey 08543-4000, United States, Email: trevor.sherwoodbms.com, haiyun.xiaobms.com

T. C. Sherwood, H.-Y. Xiao, R. G. Bhaskar, E. M. Simmons, S. Zaretsky, M. P. Rauch, R. R. Knowles, T. G. M. Dhar, J. Org. Chem., 2019, 84, 8360-8379.

DOI: 10.1021/acs.joc.9b00432

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Abstract

The organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors enable an intramolecular arene alkylation reaction. This reaction provides a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

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4CzIPN

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Key Words

tetralones, organocatalysis, photochemistry

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ID: J42-Y2019