2023
DOI: 10.1039/d2qo01821g
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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,...

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Cited by 8 publications
(4 citation statements)
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References 53 publications
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“…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 .…”
Section: Resultsmentioning
confidence: 99%
“…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 .…”
Section: Resultsmentioning
confidence: 99%
“…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.…”
Section: Intermolecular S–n Bond Formationmentioning
confidence: 99%
“…An array of elegant contributions from Malacria, Cui, Xu, Han, Zhu, and Murphy et al groups enabled these radical cascades to proceed smoothly to give quinazolinones scaffolds by virtue of transition metal (TM) or photoredox catalysis (Scheme a) . Recently, our group has demonstrated electrochemical SO 2 -insertion tandem cyclization processes of N -aryl cyanamide alkene for the preparation of functionalized cyclic N -sulfonylimines via intramolecular cyclization of iminyl radicals with tethered aromatic moieties . Nevertheless, it is still highly desirable to develop the greener and diverse iminyl radical-engaged cascade reaction by utilizing the cyano group as a radical acceptor for the construction of N-containing polycyclic frameworks from readily accessible starting materials.…”
Section: Introductionmentioning
confidence: 99%