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Palladium‐Catalyzed Negishi Cross‐Coupling Reaction of Difluoroiodomethane with Arylzinc Reagents
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- Junki Nitta
- Department of Chemical Science and Engineering School of Materials and Chemical Technology Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo 152-8552 Japan
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- Hirotaka Motohashi
- Department of Chemical Science and Engineering School of Materials and Chemical Technology Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo 152-8552 Japan
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- Kohsuke Aikawa
- Department of Chemical Science and Engineering School of Materials and Chemical Technology Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo 152-8552 Japan
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- Koichi Mikami
- Department of Chemical Science and Engineering School of Materials and Chemical Technology Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo 152-8552 Japan
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Description
<jats:title>Abstract</jats:title><jats:p>The catalytic difluoromethylation of arylzinc reagents with difluoroiodomethane in the presence of Pd<jats:sub>2</jats:sub>(dba)<jats:sub>3</jats:sub>/Xantphos is described to produce difluoromethyl products. Mechanistic investigations reveal that the oxidative addition of difluoroiodomethane to [(Xantphos)Pd<jats:sup>0</jats:sup>] provides <jats:italic>trans</jats:italic>‐[(Xantphos)Pd<jats:sup>II</jats:sup>(I)CF<jats:sub>2</jats:sub>H], which is subsequently transformed to <jats:italic>cis</jats:italic>‐[(Xantphos)Pd<jats:sup>II</jats:sup>(Ph)CF<jats:sub>2</jats:sub>H] through transmetalation of phenylzinc. Next, reductive elimination occurs (<jats:italic>t</jats:italic><jats:sub>1/2</jats:sub>=44.7 min at −10 °C) to give PhCF<jats:sub>2</jats:sub>H. The structural changes in [(Xantphos)Pd<jats:sup>II</jats:sup>(Ph)CF<jats:sub>2</jats:sub>H] from <jats:italic>trans</jats:italic> to <jats:italic>cis</jats:italic> facilitates reductive elimination of PhCF<jats:sub>2</jats:sub>H.</jats:p>
Journal
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- Asian Journal of Organic Chemistry
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Asian Journal of Organic Chemistry 8 (5), 698-701, 2019-04-16
Wiley
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Details 詳細情報について
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- CRID
- 1360567179848385920
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- ISSN
- 21935815
- 21935807
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- Article Type
- journal article
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- Data Source
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- Crossref
- KAKEN
- OpenAIRE
