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

Ryan T McGuire; Connor M Simon; Arun A Yadav; Michael J Ferguson; Mark Stradiotto

doi:10.1002/anie.202002392

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

Angew Chem Int Ed Engl. 2020 Jun 2;59(23):8952-8956. doi: 10.1002/anie.202002392. Epub 2020 Mar 30.

Authors

Ryan T McGuire¹, Connor M Simon¹, Arun A Yadav², Michael J Ferguson³, Mark Stradiotto¹

Affiliations

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.

PMID: 32162451
DOI: 10.1002/anie.202002392

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.

Keywords: amination; cross-coupling; ligand design; nickel; sulfonamides.

Publication types

Research Support, Non-U.S. Gov't