期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 40, 页码 15062-15070出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja404566v
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资金
- National Science Foundation [1112456, OCI-1053575]
- Extreme Science and Engineering Discovery Environment (XSEDE)
- NSF IGERT program
- Rutgers-Jilin exchange program
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1112456] Funding Source: National Science Foundation
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 Bronsted 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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