Functionalization of C–H Bonds via Metal-Catalyzed Desulfitative Coupling: An Alternative Tool for Access to Aryl- or Alkyl-Substituted (Hetero)arenes

Abstract

International audienc

Ni(II)-Catalyzed Sulfonylation of ortho C–H Bonds in Aromatic Amides Utilizing an N,N-Bidentate Directing Group

“…In particular, the reaction of 1-naphthamides 1g1k gave the corresponding sulfides in up to 10% yield. Metal-catalyzed desulfitative coupling of CH bonds with arylsulfonyl chlorides has been extensively studied; 12 however, such a reaction was not observed in our experiment.…”

Pyrazole‐3‐carboxylates assisted N‐heterocyclic carbene palladium complexes: synthesis, characterization, and catalytic activities towards arylation of azoles with arylsulfonyl hydrazides

“…Meanwhile, Wang reported the Pd‐catalyzed desulfitative arylation of azoles using sodium arylsulfinates as aryl sources . Moreover, Soulé and Doucet have comprehensively summarized the Pd‐catalyzed desulfitative arylation of azoles using RSO 2 R′ derivatives as aryl sources . Despite these successes, the limitations of these reagents have been noted, such as high catalyst loading and excess ancillary ligand.…”

Desulfinative palladium‐catalyzed cross‐coupling of arylsulfonyl hydrazides with aryl bromides under air

“…Recently, aryl−aryl bond formation via C−S bond cleavage has attracted considerable attention, and versatile activated C−S bond‐containing partners, such as aryl sulfonyl reagents, have been explored in cross‐coupling reactions under transition metal catalysis. Commercial aryl sulfonyl halides, sulfinates and hydrazines are recognized as the new aryl sources that have been universally utilized in desulfinative arylation reactions recently (Scheme ) …”