Nickel(IV)-Catalyzed C–H Trifluoromethylation of (Hetero)arenes | Zendy

Elizabeth A. Meucci | Zendy; Shay N. Nguyen | Zendy; Nicole M. Camasso | Zendy; Eugene Chong | Zendy; Alireza Ariafard | Zendy; Allan J. Canty | Zendy; Melanie S. Sanford | Zendy

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Nickel(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.

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