Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides

Kevin M. Arendt, Abigail G. Doyle

Research output: Contribution to journalArticle

60 Scopus citations

Abstract

A new substrate class for nickel-catalyzed C(sp3) cross-coupling reactions is reported. α-Oxy radicals generated from benzylic acetals, TMSCl, and a mild reductant can participate in chemoselective cross-coupling with aryl iodides using a 2,6-bis(N-pyrazolyl)pyridine (bpp)/Ni catalyst. The mild, base-free conditions are tolerant of a variety of functional groups on both partners, thus representing an attractive C-C bond-forming approach to dialkyl ether synthesis. Characterization of a [(bpp)NiCl] complex relevant to the proposed catalytic cycle is also described.

Original languageEnglish (US)
Pages (from-to)9876-9880
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number34
DOIs
StatePublished - Aug 1 2015

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • cross-coupling
  • ethers
  • nickel
  • radicals
  • synthetic methods

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