A rhodium(III)-catalyzed tunable coupling reaction of indole derivatives with alkylidenecyclopropanes via C–H activation

Ruixing Liu; Yin Wei; Min Shi

doi:10.1039/C9CC03134K

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A rhodium(iii)-catalyzed tunable coupling reaction of indole derivatives with alkylidenecyclopropanes via C–H activation†

Ruixing Liu,^a Yin Wei

^a and Min Shi

*^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: mshi@sioc.ac.cn

^b Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, Guangdong 518000, China

Abstract

We herein report a rhodium(III)-catalyzed cross coupling of indole derivatives with alkylidenecyclopropanes (ACPs) in the presence of KCl, affording the alkene products exclusively with E-selectivity via C–H bond activation. The beta-H elimination to afford the conjugated diene derivatives has been suppressed by the addition of KCl. A plausible reaction mechanism has been proposed along with derivatization of the obtained product to demonstrate the practical usefulness of this synthetic protocol.

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DOI: https://doi.org/10.1039/C9CC03134K
Article type: Communication
Submitted: 23 Apr 2019
Accepted: 04 Jun 2019
First published: 04 Jun 2019

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Chem. Commun., 2019,55, 7558-7561

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A rhodium(III)-catalyzed tunable coupling reaction of indole derivatives with alkylidenecyclopropanes via C–H activation

R. Liu, Y. Wei and M. Shi, Chem. Commun., 2019, 55, 7558 DOI: 10.1039/C9CC03134K

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Chemical Communications

A rhodium(iii)-catalyzed tunable coupling reaction of indole derivatives with alkylidenecyclopropanes via C–H activation†

Abstract

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A rhodium(III)-catalyzed tunable coupling reaction of indole derivatives with alkylidenecyclopropanes via C–H activation

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