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Type: Journal article
Title: Mild and selective base-free C–H arylation of heteroarenes: experiment and computation
Author: Gemoets, H.P.L.
Kalvet, I.
Nyuchev, A.V.
Erdmann, N.
Hessel, V.
Schoenebeck, F.
Noël, T.
Citation: Chemical Science, 2017; 8(2):1046-1055
Publisher: Royal Society of Chemistry
Issue Date: 2017
ISSN: 2041-6520
Statement of
Hannes P.L. Gemoets, Indrek Kalvet, Alexander V. Nyuchev, Nico Erdmann, Volker Hessel, Franziska Schoenebeck and Timothy Noël
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.
Rights: This journal is © The Royal Society of Chemistry 2017
DOI: 10.1039/c6sc02595a
Grant ID: 713.013.001
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