Nickel-Catalyzed Cross-Coupling of Sulfonamides With (Hetero)aryl Chlorides |
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| Authors: | Ryan T McGuire Connor M Simon Dr Arun A Yadav Dr Michael J Ferguson Prof Dr Mark Stradiotto |
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| Institution: | 1. Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4R2 Canada;2. Paraza Pharma, Inc., 2525 Avenue Marie-Curie, Montreal, Quebec, H4S 2E1 Canada;3. X-Ray Crystallography Laboratory, Department of Chemistry University of Alberta, Edmonton, Alberta, T6G 2G2 Canada |
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| 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)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. |
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| Keywords: | amination cross-coupling ligand design nickel sulfonamides |
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