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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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Publication details

The article was received on 14 Jun 2016, accepted on 01 Sep 2016 and first published on 05 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC02595A
Citation: Chem. Sci., 2017,8, 1046-1055
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    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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