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Pd-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Unactivated Olefins by a Heck Reaction/Enolate
Roshan K Dhungana1, Bijay Shrestha1, Rajani Thapa-Magar1
1Department of Chemistry & Chemical Biology, The University of New Mexico , Albuquerque, New Mexico 87131, United States.
Abstract:
We disclose a Pd-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with aryl iodides and tethered enolates. The current method allows the rapid synthesis of a variety of 1,3,4-trisubstituted pyrrolidinones from simple and readily available amides. We further demonstrate this new method's application by postsynthetically modifying the arylacetic acid side chains of two commercial nonsteroidal anti-inflammatory drugs, indomethacin and tolmetin, to highly decorated 4-benzylpyrrolidinone frameworks. Mechanistic studies reveal that the reaction proceeds via a Heck reaction/enolate cyclization cascade, a process that exploits β-H elimination in a constructive mode for regioselective 1,2-difunctionalization of unactivated olefins.