Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration

Korkis, Stamatis E.; Burns, David J.; Lam, Hon Wai

Abstract

The Rh(III)-catalyzed oxidative C–H allylation of N-acetylbenzamides with 1,3-dienes is described. The presence of allylic hydrogens cis- to the less substituted alkene of the 1,3-diene is important for the success of these reactions. With the assistance of reactions using deuterated 1,3-dienes, a proposed mechanism is provided. The key step is postulated to be the first reported examples of allyl-to-allyl 1,4-Rh(III) migration.

Citation

Korkis, S. E., Burns, D. J., & Lam, H. W. (in press). Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration. Journal of the American Chemical Society, https://doi.org/10.1021/jacs.6b06884

• Journal Article Type: Article
• Acceptance Date: Aug 21, 2016
• Online Publication Date: Aug 22, 2016
• Deposit Date: Sep 5, 2016
• Publicly Available Date: Sep 5, 2016
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Electronic ISSN: 1520-5126
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• DOI: https://doi.org/10.1021/jacs.6b06884
• Public URL: https://nottingham-repository.worktribe.com/output/804872
• Publisher URL: http://pubs.acs.org/doi/abs/10.1021/jacs.6b06884
• Additional Information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/page/policy/articlesonrequest/index.html
• Contract Date: Sep 5, 2016