FeBr3-catalyzed regioselective hydroxysulfenylation of N-allylsulfonamides with sulfonyl hydrazides

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

“…Furthermore, sulfonyl hydrazides could act as precursors of electrophilic RSX (X=Br, I). Thiodiazonium, thiosulfonates or disulfides were conducted as key intermediates.…”

“…Mechanistically, addition of alkenes to RSI provided the thiiranium intermediate, which underwent nucleophilic attack by alcohols to give ring‐opening products. The Li group reported another three‐component reaction to yield β ‐hydroxysulfides (Eq. 58‐2).…”

Controllable synthesis of disulfides and thiosulfonates from sodium sulfinates mediated by hydroiodic acid using ethanol and H2O as solvents

“…The reductive coupling of sulfonyl chlorides or sulfonyl hydrazines is always used to prepare disulfides and thiosulfonates. 8–11 An efficient NaI/TBHP-mediated sulfonylation of thiols was reported by Chen et al , which provides a convenient route to thiosulfonates with wide functional group compatibility. 12 Shyam and co-workers found that BF 3 ·OEt 2 -mediated disproportionate coupling reaction of sodium sulfinates which was an efficient approach to obtain symmetrical and unsymmetrical thiosulfonates.…”

Palladium-Catalyzed Intramolecular Allylic Amidation via Decarboxylative Aromatization: Synthesis of N-Allyl-N-aryl Sulfonamides

“…To further demonstrate the synthetic utility of N -allyl- N -aryl sulfonamide products, two follow-up transformations were performed, as shown in Scheme . We first submitted N -allyl- N -aryl sulfonamide 4a under the conditions of PdCl 2 , Li 2 CO 3 , and CuBr, leading to the formation of 4-aryl-1,2,3,4-tetrahydroquinoline 7 which can be transformed into bioactives. , In addition, a bioactive nitrogen-containing β-hydroxysulfide 8 can also be readily obtained using 4a and heating it with sulfonyl hydrazides in the presence of FeBr 3 -bpy and Na 2 S 2 O 8 . , …”