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

Autor: Lee HJ; Department of Chemistry, College of Science, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul, 02841, Republic of Korea.; Samsung Advanced Institute of Technology, 130 Samsung-ro, Yeongtong-gu, Suwon-si, Gyeonggi-do, 16678, Republic of Korea., Joo JU; Department of Chemical Engineering, Pohang University of Science and Technology, 77 Cheongam-ro, Nam-gu, Pohang-si, Gyeongsangbuk-do, 37673, Republic of Korea., Yim SJ; Department of Chemical Engineering, Pohang University of Science and Technology, 77 Cheongam-ro, Nam-gu, Pohang-si, Gyeongsangbuk-do, 37673, Republic of Korea., Kim DP; Department of Chemical Engineering, Pohang University of Science and Technology, 77 Cheongam-ro, Nam-gu, Pohang-si, Gyeongsangbuk-do, 37673, Republic of Korea. dpkim@postech.ac.kr., Kim H; Department of Chemistry, College of Science, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul, 02841, Republic of Korea. heejinkim@korea.ac.kr.
Jazyk: angličtina
Zdroj: Nature communications [Nat Commun] 2023 Mar 03; Vol. 14 (1), pp. 1231. Date of Electronic Publication: 2023 Mar 03.
DOI: 10.1038/s41467-022-35611-9
Abstrakt: Fluoroform (CF 3 H) is the simplest reagent for nucleophilic trifluoromethylation intermediated by trifluoromethyl anion (CF 3 - ). However, it has been well-known that CF 3 - 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 CF 3 - 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 CF 3 H 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 CF 3 - , extending to the multi-gram-scale synthesis of valuable compounds by 1-hour operation of the integrated flow system.
(© 2023. The Author(s).)
Databáze: MEDLINE
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