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Copper‐Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate
Author(s) -
Wu Wei,
Tian Qinli,
Chen Taotao,
Weng Zhiqiang
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604300
Subject(s) - trifluoromethyl , ketone , chemistry , aryl , copper , halide , organic chemistry , reaction mechanism , medicinal chemistry , catalysis , alkyl
A copper‐mediated trifluoroacetylation of various arenediazonium salts with ethyl trifluoropyruvate is reported. The reaction proceeded smoothly under mild conditions at room temperature giving trifluoromethyl aryl ketones in moderate to good yields. A variety of functional groups, including methoxy, hydroxy, ester, ketone, trifluoromethyl, and halide groups, were well tolerated. A possible reaction mechanism involving an aryl radical intermediate was proposed and supported by experimental evidence. This reaction provides a new route to trifluoromethyl aryl ketones, notable synthetic targets, from the corresponding anilines.