Nickel-Catalyzed Cross-Coupling of Sulfonamides With (Hetero)aryl Chlorides

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作者
McGuire, Ryan T. [1 ]
Simon, Connor M. [1 ]
Yadav, Arun A. [2 ]
Ferguson, Michael J. [3 ]
Stradiotto, Mark [1 ]
机构
[1] Department of Chemistry, Dalhousie University, Halifax,NS,B3H 4R2, Canada
[2] Paraza Pharma, Inc., 2525 Avenue Marie-Curie, Montreal,QC,H4S 2E1, Canada
[3] X-Ray Crystallography Laboratory, Department of Chemistry University of Alberta, Edmonton,AB,T6G 2G2, Canada
关键词
The development of Ni-catalyzed C−N crosscouplings 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)NEt2) 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. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA; Weinheim;
D O I
10.1002/ANGE.202002392
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页码:9037 / 9041
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