Photocatalytic defluoroalkylation and hydrodefluorination of trifluoromethyls using o-phosphinophenolate

Can Liu, Ni Shen and Rui Shang ()
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Can Liu: University of Science and Technology of China
Ni Shen: University of Science and Technology of China
Rui Shang: University of Science and Technology of China

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Under visible light irradiation, o-phosphinophenolate functions as an easily accessible photoredox catalyst to activate trifluoromethyl groups in trifluoroacetamides, trifluoroacetates, and trifluoromethyl (hetero)arenes to deliver corresponding difluoromethyl radicals. It works in relay with a thiol hydrogen atom transfer (HAT) catalyst to enable selective defluoroalkylation and hydrodefluorination. The reaction allows for the facile synthesis of a broad scope of difluoromethylene-incorporated carbonyl and (hetero)aromatic compounds, which are valuable fluorinated intermediates of interest in the pharmaceutical industry. The ortho-diphenylphosphino substituent, which is believed to facilitate photoinduced electron transfer, plays an essential role in the redox reactivity of phenolate. In addition to trifluoromethyl groups, pentafluoroethyl groups could also be selectively defluoroalkylated.

Date: 2022
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DOI: 10.1038/s41467-022-28007-2

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