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Issue 1, 2019
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Theoretical studies on Rh(iii)-catalyzed regioselective C–H bond cyanation of indole and indoline

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Abstract

Density functional theory calculations were carried out to study the reaction mechanism of the Rh(III)-catalyzed regioselective C–H cyanation of indole and indoline with N-cyano-N-phenyl-para-methylbenzenesulfonamide (NCTS). This mechanism involves four major steps: C–H activation, cyano group insertion, β-N elimination, and regeneration of active species. How different indole and indoline substrates affect the regioselectivity of C–H bond cyanation has been examined and analyzed in detail. Our calculation results indicate that the regioselectivity of C–H bond cyanation of indole depends on the nucleophilicity of carbon atoms in C–Rh(III) bonds to the cyano group. For indoline, it can be attributed to the different hybridization platforms of the C–H bond activation.

Graphical abstract: Theoretical studies on Rh(iii)-catalyzed regioselective C–H bond cyanation of indole and indoline

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Supplementary files

Article information


Submitted
11 Oct 2018
Accepted
21 Nov 2018
First published
23 Nov 2018

Dalton Trans., 2019,48, 168-175
Article type
Paper

Theoretical studies on Rh(III)-catalyzed regioselective C–H bond cyanation of indole and indoline

C. Deng, Y. Sun, Y. Ren and W. Zhang, Dalton Trans., 2019, 48, 168
DOI: 10.1039/C8DT04079F

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