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 journalArticle

37 Citations (Scopus)

Abstract

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
Volume135
Issue number40
DOIs
Publication statusPublished - Oct 21 2013

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Olefin hydroaryloxylation catalyzed by pincer-iridium complexes'. Together they form a unique fingerprint.

  • Cite this

    Haibach, M. C., Guan, C., Wang, D. Y., Li, B., Lease, N., Steffens, A. M., Krogh-Jespersen, K., & Goldman, A. S. (2013). Olefin hydroaryloxylation catalyzed by pincer-iridium complexes. Journal of the American Chemical Society, 135(40), 15062-15070. https://doi.org/10.1021/ja404566v