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

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 p...

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Main Authors: Korkis, Stamatis E., Burns, David J., Lam, Hon Wai
Format: Article
Published: American Chemical Society 2016
Online Access:https://eprints.nottingham.ac.uk/36246/
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author Korkis, Stamatis E.
Burns, David J.
Lam, Hon Wai
author_facet Korkis, Stamatis E.
Burns, David J.
Lam, Hon Wai
author_sort Korkis, Stamatis E.
building Nottingham Research Data Repository
collection Online Access
description 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.
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spelling nottingham-362462020-05-04T18:06:15Z https://eprints.nottingham.ac.uk/36246/ 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 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. American Chemical Society 2016-08-22 Article PeerReviewed Korkis, Stamatis E., Burns, David J. and Lam, Hon Wai (2016) 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 . ISSN 1520-5126 http://pubs.acs.org/doi/abs/10.1021/jacs.6b06884 doi:10.1021/jacs.6b06884 doi:10.1021/jacs.6b06884
spellingShingle Korkis, Stamatis E.
Burns, David J.
Lam, Hon Wai
Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration
title Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration
title_full Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration
title_fullStr Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration
title_full_unstemmed Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration
title_short Rhodium-catalyzed oxidative C–H allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-Rh(III) migration
title_sort rhodium-catalyzed oxidative c–h allylation of benzamides with 1,3-dienes by allyl-to-allyl 1,4-rh(iii) migration
url https://eprints.nottingham.ac.uk/36246/
https://eprints.nottingham.ac.uk/36246/
https://eprints.nottingham.ac.uk/36246/