Olefin hydroaryloxylation catalyzed by pincer-iridium complexes.

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2013
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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.
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haibach2013olefinjournal Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Michael C Haibach, Changjian Guan, David Y Wang, Bo Li, Nicholas Lease, Andrew M Steffens, Karsten Krogh-Jespersen, Alan S Goldman
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Journal Journal of the American Chemical Society
Year 2013
DOI
10.1021/ja404566v
URL
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