2022
DOI: 10.1039/d2sc04027a
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Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry

Abstract: Sulfonyl radical mediated process has been considered as a powerful strategy for the construction of sulfonyl compounds. However, the efficient and high atom-economical radical approach to sulfonate esters is still...

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Cited by 30 publications
(13 citation statements)
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“…Based on these experimental results and the previous reports, 3 a , b ,9 a possible reaction pathway is proposed in Scheme 7. The anodic oxidation of 2a generated the Ts radical which attacked the alkene moiety of 1aa to give intermediate Ia .…”
Section: Introductionsupporting
confidence: 67%
See 1 more Smart Citation
“…Based on these experimental results and the previous reports, 3 a , b ,9 a possible reaction pathway is proposed in Scheme 7. The anodic oxidation of 2a generated the Ts radical which attacked the alkene moiety of 1aa to give intermediate Ia .…”
Section: Introductionsupporting
confidence: 67%
“…8 c , d However, the development of a more sustainable and flexible approach enabling facile concomitant incorporation of SO 2 and other useful functional groups from easy-to-handle SO 2 surrogates and available starting materials to streamline the assembly of high value-added fused sultams is still unexplored. 9…”
Section: Introductionmentioning
confidence: 99%
“…The method included treatment of combination of methanol and sodium metabisulfite with alkenols 39 a in an electrolytic cell consisting carbon (anode) and platinum (cathode) electrode for the synthesis of ketones 39 b in good yield (Scheme 39). [67] The depicted mechanism included generation of sulfite radical anion at the anode via oxidation, which upon combination with alcohol generated alkoxy sulfonyl radical Int-39 c. The alkoxy sulfonyl radical Int-39 c upon addition to Although, both the photocatalytic and electrocatalytic radical polar-cross over mainly involves a oxidation process to push the radical to the corresponding carbocation, still there are some notable difference. One of the differences could be the source of energy, in case of former it is the photon (sometimes uncontrolled) and electricity (controlled).…”
Section: Electrocatalytic Radical-polar Crossovermentioning
confidence: 99%
“…In addition to diazonium salts, thianthrenium salts which could be utilized as both aryl and alkyl radical precursors were also compatible with this multicomponent reaction. Additionally, NaHSO 3 was employed as the SO 2 surrogate in the electrochemical three‐component reaction between alcohols and alkenes to construct sulfonate esters [64] …”
Section: Multicomponent Sulfonylation Involving Other So2 Surrogatesmentioning
confidence: 99%