Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 13, Pages 6639-6648Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00781
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Funding
- Office of Basic Energy Sciences of the U.S. Department of Energy [DE-FG02-13ER16369]
- Sichuan University of Science Engineering [2012RC17]
- Zigong Science and Technology Bureau [2013X02]
- Education Department of Sichuan Province [14ZB0207]
- Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education [LZJ1401]
- China Scholarship Council [201408510085]
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A mild and practical protocol for manganese-catalyzed aerobic oxytrifluoromethylation of olefinic bonds of styrene derivatives using CF3SO2Na (Langlois' reagent) as the CF3 source is described. A distinguishing feature of this method is the generation of trifluoromethyl radicals from CF3SO2Na using the simple manganese salt/O-2 system. The reaction proceeds under ambient conditions, free of added peroxide initiators, and provides moderate to good selectivities for alcohol versus ketone product.
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