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
    • Chemical and Synthetic Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States
    • §Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States

    An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

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