title: Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions.
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.
authors.affiliation: Department of Chemistry, University of Minnesota-Twin Cities , 207 Pleasant St. SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Giang T
authors.initials: GT
authors.lastname: Hoang
authors.affiliation: Department of Chemistry, University of Minnesota-Twin Cities , 207 Pleasant St. SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Dylan J
authors.initials: DJ
authors.lastname: Walsh
authors.affiliation: Department of Chemistry, University of Minnesota-Twin Cities , 207 Pleasant St. SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Kathryn A
authors.initials: KA
authors.lastname: McGarry
authors.affiliation: Department of Chemistry, University of Minnesota-Twin Cities , 207 Pleasant St. SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Constance B
authors.initials: CB
authors.lastname: Anderson
authors.affiliation: Department of Chemistry, University of Minnesota-Twin Cities , 207 Pleasant St. SE, Minneapolis, Minnesota 55455, United States.
authors.forename: Christopher J
authors.identifier: 0000-0002-1904-6135
authors.initials: CJ
authors.lastname: Douglas