Olefin hydroaryloxylation catalyzed by pincer-iridium complexes

Michael C. Haibach, Changjian Guan, David Y. Wang, Bo Li, Nicholas Lease, Andrew M. Steffens, Karsten Krogh-Jespersen, Alan S. Goldman

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)


Aryl alkyl ethers, which are widely used throughout the chemical industry, are typically produced via the Williamson ether synthesis. Olefin hydroaryloxylation potentially offers a much more atom-economical alternative. Known acidic catalysts for hydroaryloxylation, however, afford very poor selectivity. We report the organometallic-catalyzed intermolecular hydroaryloxylation of unactivated olefins by iridium "pincer" complexes. These catalysts do not operate via the hidden Brønsted acid pathway common to previously developed transition-metal-based catalysts. The reaction is proposed to proceed via olefin insertion into an iridium-alkoxide bond, followed by rate-determining C-H reductive elimination to yield the ether product. The reaction is highly chemo- and regioselective and offers a new approach to the atom-economical synthesis of industrially important ethers and, potentially, a wide range of other oxygenates.

Original languageEnglish
Pages (from-to)15062-15070
Number of pages9
JournalJournal of the American Chemical Society
Issue number40
Publication statusPublished - Oct 21 2013

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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