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Issue 2, 2017
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Mild and selective base-free C–H arylation of heteroarenes: experiment and computation

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Abstract

A mild and selective C–H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck–Matsuda type coupling mechanism.

Graphical abstract: Mild and selective base-free C–H arylation of heteroarenes: experiment and computation

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Article information


Submitted
14 Jun 2016
Accepted
01 Sep 2016
First published
05 Sep 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 1046-1055
Article type
Edge Article

Mild and selective base-free C–H arylation of heteroarenes: experiment and computation

H. P. L. Gemoets, I. Kalvet, A. V. Nyuchev, N. Erdmann, V. Hessel, F. Schoenebeck and T. Noël, Chem. Sci., 2017, 8, 1046
DOI: 10.1039/C6SC02595A

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