Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF 2 H-Substituted Polycyclic Imidazoles.

Autor: Lin SN; College of Chemistry and Environment Science, Shangrao Normal University, Shangrao 334001, China., Deng Y; College of Chemistry and Environment Science, Shangrao Normal University, Shangrao 334001, China., Zhong H; College of Chemistry and Environment Science, Shangrao Normal University, Shangrao 334001, China., Mao LL; College of Chemistry and Environment Science, Shangrao Normal University, Shangrao 334001, China., Ji CB; College of Chemistry and Environment Science, Shangrao Normal University, Shangrao 334001, China., Zhu XH; College of Chemistry and Environment Science, Shangrao Normal University, Shangrao 334001, China., Zhang X; College of Chemistry and Environment Science, Shangrao Normal University, Shangrao 334001, China., Yang BM; Joint School of National University of Singapore and Tianjin University, Fuzhou 350207, China.
Jazyk: angličtina
Zdroj: ACS omega [ACS Omega] 2024 Jun 19; Vol. 9 (26), pp. 28129-28143. Date of Electronic Publication: 2024 Jun 19 (Print Publication: 2024).
DOI: 10.1021/acsomega.4c01177
Abstrakt: An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible and bench-stable difluoromethyltriphenylphosphonium bromide as the precursor of the -CF 2 H group has been developed to afford CF 2 H-substituted polycyclic imidazoles in moderate to good yields. This strategy, along with the construction of Csp 3 -CF 2 H/C-C bonds, is distinguished by mild conditions, no requirement of additives, simple operation, and wide substrate scope. In addition, the mechanistic experiments have indicated that the difluoromethyl radical pathway is essential for the methodology.
Competing Interests: The authors declare no competing financial interest.
(© 2024 The Authors. Published by American Chemical Society.)
Databáze: MEDLINE
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