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Mechanistic insight into the C7-selective C−H functionalization of N-acyl indole catalyzed by rhodium complex: a theoretical study

Abstract

The reaction mechanisms on the rhodium-catalyzed regioselective C7-functionalization of N-acyl indole have been theoretically investigated by employing the density functional theory (DFT) calculations. The role of the additive AgNTf2 in enhancing the reactivity and selectivity for the reaction of C7−H functionalization of N-acyl indole is clarified through our calculations. The origins of substituent group at 6-position of N-acyl indole impacting on the regioselectivity are explored by analyzing the electron and steric effects. 7-olefination product is preferred for the H-substituted substrate (reaction A), which could be attributed to the greater nucleophilicity of C7 atom in comparison to that of C2 atom. This would facilitate the subsequent electrophilic attack of Rh center. In reaction B with CF3-substituted substrate, 2-olefination product is preferred over the 7-olefination product mainly because the stronger steric effects in TS2(C7)F compared with that in TS2(C2)F.

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Publication details

The article was received on 05 Oct 2017, accepted on 06 Nov 2017 and first published on 07 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00911A
Citation: Org. Chem. Front., 2017, Accepted Manuscript
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    Mechanistic insight into the C7-selective C−H functionalization of N-acyl indole catalyzed by rhodium complex: a theoretical study

    L. Han, X. Ma, Y. Liu, Z. Yu and T. Liu, Org. Chem. Front., 2017, Accepted Manuscript , DOI: 10.1039/C7QO00911A

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