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. 2016 Sep 21;138(37):12252-7.
doi: 10.1021/jacs.6b06884. Epub 2016 Sep 6.

Rhodium-Catalyzed Oxidative C-H Allylation of Benzamides with 1,3-Dienes by Allyl-to-Allyl 1,4-Rh(III) Migration

Stamatis E Korkis  1 , David J Burns  1 , Hon Wai Lam  1
Affiliations

Rhodium-Catalyzed Oxidative C-H Allylation of Benzamides with 1,3-Dienes by Allyl-to-Allyl 1,4-Rh(III) Migration

Stamatis E Korkis et al. J Am Chem Soc. .

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.

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