Mild and selective base-free C–H arylation of heteroarenes: experiment and computation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02595a Click here for additional data file.

نویسندگان

  • Hannes P. L. Gemoets
  • Indrek Kalvet
  • Alexander V. Nyuchev
  • Nico Erdmann
  • Volker Hessel
  • Franziska Schoenebeck
  • Timothy Noël
چکیده

Amild 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.

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A new face of phenalenyl-based radicals in the transition metal-free C–H arylation of heteroarenes at room temperature: trapping the radical initiator via C–C σ-bond formation† †Electronic supplementary information (ESI) available. CCDC 1520738. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02661g Click here for additional data file. Click here for additional data file.

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017