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

102 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

Access to Document

10.1021/jacs.9b06383

Cite this

@article{e875ff192fb04d81b4f2d8c17604f6f9,

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.\}",

note = "{\textcopyright} 2019 The Authors",

year = "2019",

month = aug,

day = "14",

doi = "10.1021/jacs.9b06383",

language = "English",

volume = "141",

pages = "12872--12879",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "32",

}

TY - JOUR

T1 - Nickel(IV)-Catalyzed C-H Trifluoromethylation of (Hetero)arenes

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

C2 - 31379153

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this