In:
Angewandte Chemie International Edition, Wiley, Vol. 61, No. 40 ( 2022-10-04)
Abstract:
Direct C−H trifluoromethylation of arenes and heteroarenes poses an important synthetic challenge that is highly desirable. High‐valent Cu III −CF 3 compounds have often been invoked in copper‐mediated trifluoromethylation reactions, but the fundamental reactivity toward arenes is elusive. Herein, direct C−H trifluoromethylation of arenes/heteroarenes by a high‐valent Cu III −CF 3 compound is disclosed for the first time. The Cu III −CF 3 compound serves CF 3 radical and a Cu II oxidant by homolytic cleavage of a Cu III −CF 3 bond, which engage synergistically in a S E Ar type reaction with arenes. The presence of K 2 S 2 O 8 co‐oxidant can significantly improve the reaction yields. This reaction shows good efficiency, broad functional group tolerance, and the potential in late‐stage functionalization. The reactivity of high‐valent Cu III −CF 3 compounds disclosed in this study represents an important progress in organofluorine and Cu III chemistry.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.202209029
Language:
English
Publisher:
Wiley
Publication Date:
2022
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7
