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Nickel‐Catalyzed N‐Arylation of Fluoroalkylamines
Author(s) -
McGuire Ryan T.,
Yadav Arun A.,
Stradiotto Mark
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202014340
Subject(s) - catalysis , electrophile , aniline , nickel , halide , chemistry , aryl , combinatorial chemistry , phenol , decomposition , base (topology) , medicinal chemistry , organic chemistry , mathematical analysis , alkyl , mathematics
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, NaO t Bu), 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.