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 StatesRead the publication that featured this abstract
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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