Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions
Giang T Hoang1, Dylan J Walsh1, Kathryn A McGarry1
1Department of Chemistry, University of Minnesota-Twin Cities , 207 Pleasant St. SE, Minneapolis, Minnesota 55455, United States.
Abstract:
The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.
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