Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 6, Issue 1, Pages 1327-1335Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.7b03673
Keywords
Halides; Diaryliodonium; Aryldiazonium; alpha-Diazo carbonyls; Environment-benign; Trifluoromethylselenolation
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Funding
- Wuhan University of Technology
- Army Medical University
- Fundamental Research Funds for the Central Universities
- National Natural Science Foundation of China [21602165]
- Chutian Scholar Program from Department of Education of Hubei Province (China)
- Hundred Talent Program of Hubei Province
- Wuhan Youth Chen-Guang Project [2016070204010113]
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Environment-benign trifluoromethylselenolation of alkyl halides, electron-deficient aryl halides, diaryliodonium triflates, aryldiazonium tetrafluoroborates, and alpha-diazo carbonyls with the readily accessible [Me4N] [SeCF3] salt is described. A large number of structurally diversified substrates, previously trifluoromethylselenolated by metal-SeCF3 complex or under metal mediated catalysis at elevated temperatures, were smoothly converted in this reaction at room temperature or -40 degrees C to room temperature without using any catalyst or additive. Yields of the reactions were comparative to or even higher than those of the early reports employing transition metal catalysts. Compared to the known means, advantages of this method include simplicity, sustainability, high speed, low reaction temperatures, mild reaction conditions, a wide range of substrates, and good functional group tolerance. This catalyst- and additive-free protocol allows a mild and straightforward synthesis of various trifluoromethyl selenoethers and demonstrates the possibility of trifluoromethylselenolation with [Me4N] [SeCF3] under greener conditions.
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