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Nickel-Catalyzed N-Arylation of Fluoroalkylamines.

Authors :
McGuire RT
Yadav AA
Stradiotto M
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Feb 19; Vol. 60 (8), pp. 4080-4084. Date of Electronic Publication: 2020 Dec 23.
Publication Year :
2021

Abstract

The Ni-catalyzed N-arylation of β-fluoroalkylamines with broad scope is reported for the first time. Use of the air-stable pre-catalyst (PAd2-DalPhos)Ni(o-tol)Cl allows for reactions to be conducted at room temperature (25 °C, NaOtBu), or by use of a commercially available dual-base system (100 °C, DBU/NaOTf), to circumvent decomposition of the N-(β-fluoroalkyl)aniline product. The mild protocols disclosed herein feature broad (hetero)aryl (pseudo)halide scope (X=Cl, Br, I, and for the first time phenol-derived electrophiles), encompassing base-sensitive substrates and enantioretentive transformations, in a manner that is unmatched by any previously reported catalyst system.<br /> (© 2020 Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3773
Volume :
60
Issue :
8
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
33201556
Full Text :
https://doi.org/10.1002/anie.202014340