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

doi:10.1021/acs.joc.6b03011

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

Chemistry (Twin Cities)

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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 language	English (US)
Pages (from-to)	2972-2983
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	82
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.6b03011
State	Published - Mar 17 2017

Bibliographical note

Funding Information:
This material is based upon work supported in part by the National Science Foundation Graduate Research Fellowship Program under Grant No. 00039202. Any opinions, findings and conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the National Science Foundation.

Publisher Copyright:
© 2017 American Chemical Society.

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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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AU - Anderson, Constance B.

AU - Douglas, Christopher J.

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

Abstract

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