Mild and selective base-free C-H arylation of heteroarenes: experiment and computationElectronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02595a

Mild and selective base-free C-H arylation of heteroarenes: experiment and computationElectronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02595a

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 pal...

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Hauptverfasser: Gemoets, Hannes P. L, Kalvet, Indrek, Nyuchev, Alexander V, Erdmann, Nico, Hessel, Volker, Schoenebeck, Franziska, Noël, Timothy
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container_issue 2
container_start_page 146
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container_volume 8
creator Gemoets, Hannes P. L
Kalvet, Indrek
Nyuchev, Alexander V
Erdmann, Nico
Hessel, Volker
Schoenebeck, Franziska
Noël, Timothy
description 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. A mild and selective C-H arylation strategy for indoles, benzofurans and benzothiophenes is described.
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title Mild and selective base-free C-H arylation of heteroarenes: experiment and computationElectronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02595a
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