Manganese-Catalyzed Aerobic Oxytrifluoromethylation of Styrene Derivatives Using CF3SO2Na as the Trifluoromethyl Source

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...

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Veröffentlicht in:Journal of organic chemistry 2015-07, Vol.80 (13), p.6639-6648
Hauptverfasser: Yang, Yi, Liu, Yingle, Jiang, Yan, Zhang, Yu, Vicic, David A
Format: Artikel
Sprache:eng
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Zusammenfassung: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/O2 system. The reaction proceeds under ambient conditions, free of added peroxide initiators, and provides moderate to good selectivities for alcohol versus ketone product.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00781