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

Giang T. Hoang, Dylan J. Walsh, Kathryn A. McGarry, Constance B. Anderson, Christopher J. Douglas

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2972-2983
Number of pages12
JournalJournal of Organic Chemistry
Volume82
Issue number6
DOIs
StatePublished - Mar 17 2017

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

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