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Rhodium(III)-catalyzed chemoselective C–H functionalization of benzamides with methyleneoxetanones controlled by the solvent

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Abstract

Described herein is a Rh(III)-catalyzed and solvent-controlled double C–H functionalization of common benzamides via selective acyl C–O cleavage (β-H elimination) or alkyl C–O cleavage (β-O elimination) of the methyleneoxetanone substrate, which provides a straightforward way for the divergent synthesis of chain alkylated benzamides and seven-membered 1H-benzo[c]azepine-1,3(2H)-diones in a highly chemoselective manner. Through a series of experimental investigations together with theoretical studies, the effect of the solvent has been systematically elucidated.

Graphical abstract: Rhodium(iii)-catalyzed chemoselective C–H functionalization of benzamides with methyleneoxetanones controlled by the solvent

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Publication details

The article was received on 20 Mar 2019, accepted on 30 Apr 2019 and first published on 01 May 2019


Article type: Communication
DOI: 10.1039/C9OB00645A
Org. Biomol. Chem., 2019, Advance Article

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    Rhodium(III)-catalyzed chemoselective C–H functionalization of benzamides with methyleneoxetanones controlled by the solvent

    M. Bian, K. Ma, H. Mawjuda, X. Yu, X. Li, H. Gao, Z. Zhou and W. Yi, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00645A

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