Open AccessNickel(IV)-Catalyzed C–H Trifluoromethylation of (Hetero)arenes
Author(s) -
Elizabeth A. Meucci,
Shay N. Nguyen,
Nicole M. Camasso,
Eugene Chong,
Alireza Ariafard,
Allan J. Canty,
Melanie S. Sanford
Publication year - 2019
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b06383
Subject(s) - trifluoromethylation , chemistry , reactivity (psychology) , catalysis , nickel , stoichiometry , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , trifluoromethyl , medicine , alkyl , alternative medicine , pathology
This Article describes the development of a stable Ni IV complex that mediates C(sp 2 )-H trifluoromethylation reactions. This reactivity is first demonstrated stoichiometrically and then successfully translated to a Ni IV -catalyzed C-H trifluoromethylation of electron-rich arene and heteroarene substrates. Both experimental and computational mechanistic studies support a radical chain pathway involving Ni IV , Ni III , and Ni II intermediates.