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Nickel‐Catalyzed Cross‐Coupling of Sulfonamides With (Hetero)aryl Chlorides
Author(s) -
McGuire Ryan T.,
Simon Connor M.,
Yadav Arun A.,
Ferguson Michael J.,
Stradiotto Mark
Publication year - 2020
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.202002392
Subject(s) - aryl , nickel , catalysis , chemistry , coupling (piping) , materials science , organic chemistry , metallurgy , alkyl
Abstract The development of Ni‐catalyzed C−N cross‐couplings of sulfonamides with (hetero)aryl chlorides is reported. These transformations, which were previously achievable only with Pd catalysis, are enabled by use of air‐stable ( L )NiCl( o ‐tol) pre‐catalysts (L= PhPAd‐DalPhos and PAd2‐DalPhos ), without photocatalysis. The collective scope of (pseudo)halide electrophiles (X=Cl, Br, I, OTs, and OC(O)NEt 2 ) demonstrated herein is unprecedented for any reported catalyst system for sulfonamide C−N cross‐coupling (Pd, Cu, Ni, or other). Preliminary competition experiments and relevant coordination chemistry studies are also presented.