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Switching the site-selectivity of C–H activation in aryl sulfonamides containing strongly coordinating N-heterocycles

Abstract

The limitations of arene C–H functionalization of aryl sulfonamides containing strongly coordinating N-heterocycles were overcome using a Rh(III) catalyst. The site-selectivity of C–H carbenoid functionalization at the ortho position relative to either the sulfonamide or N-heterocycle directing groups was elegantly switched using solvent of different polarities and different additive concentrations. Importantly, sulfonamide-group-directed ortho-C–H carbenoid functionalization tolerated strongly coordinating N-heterocycles, including pyridine, pyrrole, thiazole, pyrimidine, and pyrazine. Density functional theory (DFT) calculations were performed to rationalize the reaction mechanisms and the influence of reaction polarity.

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Publication details

The article was received on 26 Jul 2019, accepted on 12 Aug 2019 and first published on 12 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03691A
Chem. Sci., 2019, Accepted Manuscript
  • Open access: Creative Commons BY license
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    Switching the site-selectivity of C–H activation in aryl sulfonamides containing strongly coordinating N-heterocycles

    Y. Dong, X. Zhang, J. Chen, W. Zou, S. Lin and H. Xu, Chem. Sci., 2019, Accepted Manuscript , DOI: 10.1039/C9SC03691A

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