2020
DOI: 10.1002/ange.202004070
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Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation

Abstract: Sulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered for radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox‐catalyzed hydrosulfonylation of electron‐deficient alkenes with sulfonyl chlorides. To increase the generality of this transformation, polarity‐reversal catalysis (PRC) was successfully implemented for alkenes bearing alkyl substituents. This … Show more

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Cited by 24 publications
(6 citation statements)
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“…In 2020, the Gouverneur group reported the first radical hydrosulfonylation of alkyls and EWG-bearing alkenes with sulfonyl chloride under visible light, using Ir­(ppy) 3 as a photocatalyst at room temperature (Scheme ). Among the various hydrogen atom donors (HADs) employed, TMS 3 SiH gave the best results. The presence of EWGs on the alkene renders the π-bond electron deficient; hence, the sulfone radical, formed by the action of the photocatalyst, readily reacts with the alkene to form a C-centered electrophilic radical (Giese addition) .…”
Section: Direct Arylsulfonylationmentioning
confidence: 99%
“…In 2020, the Gouverneur group reported the first radical hydrosulfonylation of alkyls and EWG-bearing alkenes with sulfonyl chloride under visible light, using Ir­(ppy) 3 as a photocatalyst at room temperature (Scheme ). Among the various hydrogen atom donors (HADs) employed, TMS 3 SiH gave the best results. The presence of EWGs on the alkene renders the π-bond electron deficient; hence, the sulfone radical, formed by the action of the photocatalyst, readily reacts with the alkene to form a C-centered electrophilic radical (Giese addition) .…”
Section: Direct Arylsulfonylationmentioning
confidence: 99%
“…Over the last decades, the synthetic community has been witnessing great advances in the site‐selective difunctionalization of alkenes. Among the different protocols already developed, [6–12] multicomponent strategies promoted by visible‐light photoredox catalysis emerge as very promising alternatives, owing to high synthetic efficiency and functional group tolerance, mildness, and operational simplicity [13–18] …”
Section: Introductionmentioning
confidence: 99%
“…[13][14][15][16][17][18] In this context, the photocatalytic multicomponent sulfonylation of alkenes has attracted the attention of many research groups. The interest is related to the prominent biological properties that the presence of such functional group confer to the target molecules, [15] and also for its electronic and structural properties. Once present in a given molecular framework the sulfone group can behave as a modulator of chemical reactivity of an adjacent site or as a leaving group.…”
Section: Introductionmentioning
confidence: 99%
“…First, the reaction between amines and sulfonyl chlorides occurs rapidly and is robust in scope . Second, sulfonyl chlorides themselves are valuable synthetic intermediates and can be used as a lynchpin functionality toward the synthesis of diverse sulfur containing functionalities, such as sulfonates, sulfones, sulfinates, and thiophenols . Moreover, we anticipated that a decarboxylative halosulfonylation strategy would extend to aryl sulfonyl fluorides, valuable “click” handles for sulfur­(VI)–fluoride exchange , with broad utility as chemical probes, programmable bifunctional reagents, and versatile functional handles .…”
mentioning
confidence: 99%