Convenient method for preparation of aryl sulfinates from arenes and DABSO as the SO2 surrogates

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

“…Besides transition metal-catalyzed sulfinylation, Lewis acids have been used to activate DABSO in order to unlock simple S E Ar reactivity, resulting in a formal C–H sulfinylation, affording sodium sulfinates (following the addition of a sodium base). 475…”

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…The reaction of 2-bromo-thiophene with n-BuLi at À78 C resulted in lithium-bromine exchange and nucleophilic attack by 2-lithiothiophene on BuBr; subsequent reaction with DABSO gave 5-butyl thiophenesulnate in 68% yield. Later in 2018, Wang, Zhang and co-workers 40 reported a direct and straightforward preparation of sodium arenesulnate salts from arenes and DABSO (11) in the presence of excess AlCl 3 (Scheme 10). The reaction proceeded smoothly and arenes bearing electron-donating and halide groups gave good to excellent yields.…”

“…Palladium catalyzed the sulfonylation of benzylic carbonates with sodium sulnates under the inuence of DPEphos (40) ligand in DMSO at 80 C to give benzylic sulfones. Kuwano and co-workers 366 successfully used a variety of benzylic carbonates and 1-naphthylmethyl carbonate with arenesulnates and methanesulnate to afford a broad spectrum of sulfones in high yields (Scheme 258).…”

DABSO as a SO2 gas surrogate in the synthesis of organic structures

“…24 In another protocol, sodium aryl sulfinates 3 were prepared from arenes 2 through Friedel-Crafts sulfination by treating 2 with DABSO in the presence of AlCl 3 under mild conditions (Scheme 3). 25…”