Ex-situ generation and synthetic utilization of bare trifluoromethyl anion in flow via rapid biphasic mixing

Hyune-Jea Lee, Jeong-Un Joo, Se-Jun Yim, Dong-Pyo Kim () and Heejin Kim ()
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Hyune-Jea Lee: Korea University
Jeong-Un Joo: Pohang University of Science and Technology
Se-Jun Yim: Pohang University of Science and Technology
Dong-Pyo Kim: Pohang University of Science and Technology
Heejin Kim: Korea University

Nature Communications, 2023, vol. 14, issue 1, 1-8

Abstract: Abstract Fluoroform (CF3H) is the simplest reagent for nucleophilic trifluoromethylation intermediated by trifluoromethyl anion (CF3–). However, it has been well-known that CF3– should be generated in presence of a stabilizer or reaction partner (in-situ method) due to its short lifetime, which results in the fundamental limitation on its synthetic utilization. We herein report a bare CF3– can be ex-situ generated and directly used for the synthesis of diverse trifluoromethylated compounds in a devised flow dissolver for rapid biphasic mixing of gaseous CF3H and liquid reagents that was designed and structurally optimized by computational fluid dynamics (CFD). In flow, various substrates including multi-functional compounds were chemoselectively reacted with CF3–, extending to the multi-gram-scale synthesis of valuable compounds by 1-hour operation of the integrated flow system.

Date: 2023
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DOI: 10.1038/s41467-022-35611-9

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