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

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

doi:10.1021/jacs.9b06383

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

Elizabeth A. Meucci, Shay N. Nguyen, Nicole M. Camasso, Eugene Chong, Alireza Ariafard, Allan J. Canty, Melanie S. Sanford^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

98 Citations (Scopus)

Abstract

This Article describes the development of a stable Ni^IV complex that mediates C(sp²)-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.

Original language	English
Pages (from-to)	12872-12879
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	141
Issue number	32
DOIs	https://doi.org/10.1021/jacs.9b06383
Publication status	Published - 14 Aug 2019
Externally published	Yes

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title = "Nickel(IV)-Catalyzed C-H Trifluoromethylation of (Hetero)arenes",

abstract = "This Article describes the development of a stable NiIV complex that mediates C(sp2)-H trifluoromethylation reactions. This reactivity is first demonstrated stoichiometrically and then successfully translated to a NiIV-catalyzed C-H trifluoromethylation of electron-rich arene and heteroarene substrates. Both experimental and computational mechanistic studies support a radical chain pathway involving NiIV, NiIII, and NiII intermediates.",

author = "Meucci, \{Elizabeth A.\} and Nguyen, \{Shay N.\} and Camasso, \{Nicole M.\} and Eugene Chong and Alireza Ariafard and Canty, \{Allan J.\} and Sanford, \{Melanie S.\}",

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AU - Meucci, Elizabeth A.

AU - Nguyen, Shay N.

AU - Camasso, Nicole M.

AU - Chong, Eugene

AU - Ariafard, Alireza

AU - Canty, Allan J.

AU - Sanford, Melanie S.

PY - 2019/8/14

Y1 - 2019/8/14

N2 - This Article describes the development of a stable NiIV complex that mediates C(sp2)-H trifluoromethylation reactions. This reactivity is first demonstrated stoichiometrically and then successfully translated to a NiIV-catalyzed C-H trifluoromethylation of electron-rich arene and heteroarene substrates. Both experimental and computational mechanistic studies support a radical chain pathway involving NiIV, NiIII, and NiII intermediates.

AB - This Article describes the development of a stable NiIV complex that mediates C(sp2)-H trifluoromethylation reactions. This reactivity is first demonstrated stoichiometrically and then successfully translated to a NiIV-catalyzed C-H trifluoromethylation of electron-rich arene and heteroarene substrates. Both experimental and computational mechanistic studies support a radical chain pathway involving NiIV, NiIII, and NiII intermediates.

UR - https://www.scopus.com/pages/publications/85071002612

U2 - 10.1021/jacs.9b06383

DO - 10.1021/jacs.9b06383

M3 - Article

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AN - SCOPUS:85071002612

SN - 0002-7863

VL - 141

SP - 12872

EP - 12879

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 32

ER -

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

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