Selective C-H trifluoromethoxylation of (hetero)arenes as limiting reagent

Zhijie Deng, Mingxin Zhao, Feng Wang and Pingping Tang ()
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Zhijie Deng: Nankai University
Mingxin Zhao: Nankai University
Feng Wang: Nankai University
Pingping Tang: Nankai University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract Methods for direct C-H trifluoromethoxylation of arenes and heteroarenes are rare, despite the importance of trifluoromethoxylated compounds for pharmaceuticals, agrochemicals, and material sciences. Especially selective C-H trifluoromethoxylation of pyridines remains a formidable challenge. Here we show a general late-stage C-H trifluoromethoxylation of arenes and heteroarenes as limiting reagent with trifluoromethoxide anion. The reaction is mediated by silver salts under mild reaction conditions, exhibiting broad substrate scope and wide functional-group compatibility. In addition, ortho-position selective C-H trifluoromethoxylation of pyridines is observed. The method is not only applicable to the gram-scale synthesis of trifluoromethoxylated products but also allows efficient late-stage C-H trifluoromethoxylation of marketed small-molecule drugs, common pharmacophores and natural products.

Date: 2020
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DOI: 10.1038/s41467-020-16451-x

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