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Molecules 2018, 23(7), 1582; https://doi.org/10.3390/molecules23071582

Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines

Centro de Investigaciones Científicas Avanzadas (CICA) and Departamento de Química, Universidade da Coruña, E-15071 A Coruña, Spain
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Received: 24 May 2018 / Revised: 13 June 2018 / Accepted: 26 June 2018 / Published: 29 June 2018
(This article belongs to the Special Issue Indium in Organic Synthesis)
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Abstract

The activation of C–H bonds through catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our research program devoted to the development of metal-catalyzed reactions using indium organometallics, a protocol for the C–H activation and C–C coupling of 2-arylpyridines with triorganoindium reagents under Rh(I) catalysis is reported. Under the optimized conditions, we found that Me3In and Ar3In reagents reacted with 2-arylpyridines and related compounds in the presence of Rh(PPh3)3Cl, in PhCl/THF (9:1), at 120 °C for 48 h, to afford the ortho-coupling products in moderate to good yields. The nitrogen atom in the pyridine ring acts as a directing group to assist the functionalization at the ortho position of the aryl group forming a new C–C bond at this position. View Full-Text
Keywords: C–H activation; cross-coupling reactions; rhodium-catalyzed; indium organometallics C–H activation; cross-coupling reactions; rhodium-catalyzed; indium organometallics
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Riveiros, R.; Tato, R.; Pérez Sestelo, J.; Sarandeses, L.A. Triorganoindium Reagents in Rh-Catalyzed C–H Activation/C–C Cross-Coupling Reactions of 2-Arylpyridines. Molecules 2018, 23, 1582.

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