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

• Published in: Angewandte Chemie International Edition Vol. 59; no. 23; pp. 8952 - 8956
• Main Authors: McGuire, Ryan T., Simon, Connor M., Yadav, Arun A., Ferguson, Michael J., Stradiotto, Mark
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 02.06.2020; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: amination; Antibiotics; Aromatic compounds; Catalysis; Catalysts; Chemistry; Chemistry, Multidisciplinary; Chlorides; Copper; Couplings; Cross coupling; ligand design; Nickel; Palladium; Physical Sciences; Science & Technology; Sulfonamides; HALIDES; nickel; AMMONIA; sulfonamides; BROMIDES; INDOLES; IODIDES; BISPHOSPHINES; ARYL ELECTROPHILES; cross-coupling; ligand design; amination; LIGAND; N-ARYLATION
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202002392

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. Ancillary Ligation: The development of the first nickel‐catalyzed protocols for the cross‐coupling of sulfonamides with inexpensive and abundant (hetero)aryl chlorides and phenol derivatives is enabled by use of appropriate bisphosphine ligation.