Sulfonamide Directivity Enables Ni-Catalyzed 1,2-Diarylation of Diverse Alkenyl Amines

Abstract

1,2-Diarylation of alkenyl sulfonamides with aryl iodides and aryl boronic esters under nickel catalysis is reported. The developed method tolerates coupling partners with disparate electronic properties and substitution patterns. Di- and trisubstituted alkenes as well as alkenes distal from the directing group are all accommodated. Control experiments are consistent with a N-Ni coordination mode of the directing group, which stands in contrast to a previous report on amide-directed 1,2-diarylation, which involves carbonyl coordination. The synthetic utility of the method arises from the dual function of the sulfonamide as both a directing group and a masked amine nucleophile. This is highlighted by various product diversifications where complex amine compounds are synthesized in a two-step sequence of N-functionalization and deprotection of the sulfonyl group.