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

H.P.L. Gemoets, I. Kalvet, A. Nyuchev, N. Erdmann, V. Hessel, F. Schoenebeck, T. Noël

Research output: Contribution to journalArticleAcademicpeer-review

60 Citations (Scopus)
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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.
Original languageEnglish
Article number8
Pages (from-to)1046-1055
Number of pages10
JournalChemical Science
Volume2017
Issue number2
DOIs
Publication statusPublished - 5 Sep 2016

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