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J Am Chem Soc. 2017 Sep 13;139(36):12430-12433. doi: 10.1021/jacs.7b07944. Epub 2017 Aug 30.

Silver-Catalyzed Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids.

Author information

1
Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
2
School of Materials and Chemical Engineering, Ningbo University of Technology , No. 201 Fenghua Road, Ningbo 315211, China.

Abstract

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 °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)3Me, which undergoes reductive elimination and subsequent oxidation to give Cu(CF3)2 as the active species responsible for the trifluoromethylation of alkyl radicals.

PMID:
28841304
DOI:
10.1021/jacs.7b07944

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