Litcius/Paper detail

Neutral <scp>Five‐Coordinate</scp> Arylated Copper(<scp>III</scp>) Complex: Key Intermediate in <scp>Copper‐Mediated</scp> Arene Trifluoromethylation

Guangyu Wang, Man Li, Xuebing Leng, Xiao‐Song Xue, Qilong Shen

2022Chinese Journal of Chemistry30 citationsDOI

Abstract

Comprehensive Summary Five‐coordinate neutral Cu(III) complexes have long been considered as the key intermediates in copper‐mediated/catalyzed arene trifluoromethylative reactions, but the identity of these complexes remains elusive. Herein, we reported, for the first time, the preparation and characterization of these putative complexes [(bpy)Cu(CF 3 ) 2 (C 6 F 4 R)] and investigation of their C(sp 2 )‐CF 3 bond‐forming reductive elimination. Our mechanistic studies including kinetic studies, the effect of temperature and solvents, the effect of the para ‐substitution of the ligand as well as DFT calculations suggest that C(sp 2 )‐CF 3 reductive elimination process proceeds via synchronous bond‐breaking/bond‐forming process.

Topics & Concepts

ChemistryReductive eliminationCopperLigand (biochemistry)TrifluoromethylationStereochemistryCombinatorial chemistryMedicinal chemistryCatalysisOrganic chemistryReceptorAlkylTrifluoromethylBiochemistryFluorine in Organic ChemistryInorganic Fluorides and Related Compounds