Metal-free carbon–carbon cross-couplings between the ion pairs in sulfonium tetraphenylborates

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

“…283,284 Following this transformation, the same group was able to develop a general palladium-catalyzed cross coupling of arylsulfonium salts with sodium tetraarylborates (Scheme 72c), 285 a similar transformation, albeit on specialized substrates, having been reported in a metal-free variant a year prior by Huang and co-workers. 286…”

“…In this context, in 2015, Yorimitsu and co-workers disclosed the facile transformation of dibenzothiophene ( 430 ) into triphenylenes ( 434 ), which relied on sequential double alkylation and cross coupling via alkylsulfonium salts 431 and 433 (Scheme b). , Following this transformation, the same group was able to develop a general palladium-catalyzed cross coupling of arylsulfonium salts with sodium tetraarylborates (Scheme c), a similar transformation, albeit on specialized substrates, having been reported in a metal-free variant a year prior by Huang and co-workers …”

“…283,284 Following this transformation, the same group was able to develop a general palladiumcatalyzed cross coupling of arylsulfonium salts with sodium tetraarylborates (Scheme 72c), 285 a similar transformation, albeit on specialized substrates, having been reported in a metal-free variant a year prior by Huang and co-workers. 286 In 2016, Zhang and co-workers, as well as the groups of Cowper and Lewis reported Suzuki-type cross-coupling reactions of arylsulfonium salts with arylboronic acids and esters, enabling the syntheses of biphenyls, stilbenes, 287 and arylated azulene derivatives, respectively. 288 Moreover, the Zhang group also developed Mizoroki−Heck and Sonogashiratype coupling reactions of diarylsulfonium salts (Scheme 73a).…”