Development and Mechanistic Study of Quinoline-Directed Acyl C–O Bond Activation and Alkene Oxyacylation Reactions

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.