Pd‐catalyzed ligand‐free desulfitative Heck reaction with arenesulfinic acid salts under air

Abstract

Palladium‐catalyzed cross‐coupling reactions of various aryl sulfinic acid salts with a wide variety of vinyl substrates have been achieved in good to excellent yields under simple aerobic conditions at 70°C with the assistance of Cu(II) salts. The reaction can be accelerated by the combination of DMSO with THF. The reported Matsuda–Heck type coupling reactions are tolerant to the common functional groups, making these transformations as attractive alternatives to the traditional cross‐coupling approaches. Copyright © 2013 John Wiley & Sons, Ltd.

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 ) …”

Pd‐catalyzed Desulfitative reaction of Aryltrifluoroborates with sodium Arenesulfinates in water

“…In recent years, the readily accessible sodium arylsulfinates have attracted considerable attention in organic synthesis as precursors in various cross-coupling reactions due to the easy availability and the compatibility with numerous functional groups. Interestingly, sodium arylsulfinates were also reported as the coupling partners for the Pd-catalyzed desulfitative coupling reactions, such as desulfinative Heck-type, [36][37][38] addition reactions to double or triple bonds, [39][40][41][42][43] as well as cross-coupling [44][45][46][47][48][49] and C-H arylation [50][51][52][53][54][55][56][57][58][59] reactions have been well developed. [60] Moreover, the related reaction conditions were found much milder than those reported for the corresponding aryl carboxylic acids.…”

Cu‐catalyzed coupling of arylsulfinic salts with arylsilanes under mild conditions

“…Recent studies of transition‐metal‐catalyzed transformation with arylsulfinate salts have been reported . Sodium arylsulfinate has been widely used as a kind of sulfonyl reagent with many advantages over arylsulfonyl chlorides in that it is easily handled and more stable .…”