Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 36, Pages 12430-12433Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b07944
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Funding
- National Basic Research Program of China (973 Program) [2015CB931900]
- NSFC [21421002, 21472220, 21532008, 21602239]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20020000]
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The silver-catalyzed decarboxylative trifluoromethylation of aliphatic carboxylic acids is described. With AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of aliphatic carboxylic acids with (bpy)Cu(CF3)(3) (bpy = 2,2'-bipyridine) and ZnMe2 in aqueous acetonitrile at 40 degrees C afford the corresponding decarboxylative trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl carboxylic acids and exhibits wide functional group compatibility. Mechanistic studies reveal the intermediacy of Cu(CF3)(3)Me, which undergoes reductive elimination and subsequent oxidation to give Cu(CF3)(2) as the active species responsible for the trifluoromethylation of alkyl radicals.
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