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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