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A versatile rhodium(III) catalyst for direct acyloxylation of aryl and alkenyl C–H bonds with carboxylic acids

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Abstract

Rh(III)-Catalyzed highly regioselective direct acyloxylation of sp2 C–H bonds with carboxylic acids has been developed. The catalytic system consisting of a cationic Rh(III) complex and a silver oxidant allowed a variety of arenes and alkenes bearing different directing groups (not limited to strongly coordinating N-heterocyclic directing groups) to undergo efficient acyloxylation with a broad range of readily available alkyl, alkenyl and aryl carboxylic acids, and a number of valuable functional groups in both coupling partners were well tolerated in the reaction regardless of their electronic properties and positions. This method provides a straightforward and convenient access to various valuable acyloxylated products. Furthermore, the synthetic utility of this protocol was demonstrated by the later-stage functionalization and modification of biologically active compounds. Mechanistic studies reveal the involvement of five-membered rhodacycles as key intermediates.

Graphical abstract: A versatile rhodium(iii) catalyst for direct acyloxylation of aryl and alkenyl C–H bonds with carboxylic acids

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Publication details

The article was received on 17 Sep 2017, accepted on 12 Oct 2017 and first published on 16 Oct 2017


Article type: Research Article
DOI: 10.1039/C7QO00844A
Citation: Org. Chem. Front., 2018, Advance Article
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    A versatile rhodium(III) catalyst for direct acyloxylation of aryl and alkenyl C–H bonds with carboxylic acids

    C. Chen, Y. Pan, H. Zhao, X. Xu, J. Xu, Z. Zhang, S. Xi, L. Xu and H. Li, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00844A

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