Electrochemical tandem cyclization to access sulfonylated fused sultams via SO₂ insertion with sodium metabisulfite

Abstract

An electrochemical three-component transformation between N-cyanamide alkene, Na2S2O5 and sulfonyl hydrazide was described, in which various sulfonylated fused sultams were prepared in a sustainable and modular fashion. In this process,...

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides

“…Based on the experimental results and literature reports, 9,11 we proposed a possible reaction mechanism using reactions involving 1a with 2a and 4a as an example (Scheme 3d). The sulfonyl radical precursor 4a or 2a was electrochemically oxidized at the anode to generate the sulfonyl radical A.…”

Electrochemical Synthesis of Selenosulfonates from Diselenides and Sulfonyl Hydrazides

“…Based on the above experiments and literature reports, a possible mechanism for the reaction was proposed (Figure ). First, benzene­sulfono­hydrazide 2a undergoes stepwise anodic oxidation, leading to the release of N 2 and ultimately producing the pivotal phenylsulfonyl radical IV .…”

Advances in S–N bond formation via electrochemistry: a green route utilizing diverse sulfur and nitrogen sources

“…83 Recently, Liao and co-workers presented a three-component electrochemical synthesis of sulfonylated fused sultams via SO 2 insertion from sulfonyl hydrazide, sodium metabisulfite, and N -cyanamide (Scheme 15). 84 The reaction was carried out in a simple undivided cell employing a graphite anode and cathode in the presence of methane sulfonic acid at 30 °C with a constant potential current of 1.5 V for 12 h in the absence of any electrolyte, and the sulfonylated benzosultams were obtained in moderate to good yields. Firstly, sulfonyl hydrazide was oxidized to generate a T s radical on the graphite anode surface which attacked the alkene moiety to give the intermediate.…”