Exploring the synthetic application of sulfinyl radicals

Zhang, Zixu; Wang, Xinru; Sivaguru, Paramasivam; Wang, Zikun

doi:10.1039/d2qo01403c

Cited by 11 publications

(8 citation statements)

References 101 publications

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“…The radical sulfinylation reaction is much less developed compared with radical sulfonylation, perhaps due to the lack of sufinyl-inducing reagents . Sulfinyl sulfones are known to react with nucleophiles, and more recently, Bi and Larionov showed that alkyl radicals engage in radical sulfinylation with this type of reagent . They can be readily prepared by the reaction of sulfinates with an acylating reagent.…”

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confidence: 99%

Photoinduced Radical Sulfinylation of C(sp³)–H Bonds with Sulfinyl Sulfones

et al. 2023

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A direct C(sp3)–H sulfinylation reaction of alkanes with sulfinyl sulfones via decatungstate photocatalysis is reported. The sulfinyl sulfones generated in situ from sulfinates in the presence of an acylating reagent were able to trap the alkyl radicals that were produced via the photoinduced direct hydrogen atom transfer of alkanes, leading to a range of sulfoxides. This radical sulfinylation process provides an efficient and concise method for the synthesis of sulfoxides from abundant alkanes under mild conditions. Using the same strategy, aldehydes can also be transferred to the corresponding sulfoxides via decarbonylative sulfinylation.

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confidence: 99%

Photoinduced Radical Sulfinylation of C(sp³)–H Bonds with Sulfinyl Sulfones

et al. 2023

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“…Based on the observations and previous publications, ,,, a proposed mechanism for the transformation is depicted in Scheme . It begins with an electron transfer from photoexcited 4CzIPN to NHPI ester.…”

Section: Resultsmentioning

confidence: 92%

Catalytic Decarboxylative Radical Sulfinylation

Chen

Gong

et al. 2023

J. Org. Chem.

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Sulfoxides are ubiquitous in both naturally and synthetically bioactive molecules. We report herein a redox-neutral and mild approach for radical sulfinylation of redox-active esters via dual photoredox and copper catalysis, furnishing a series of functionalized sulfoxides. The reaction could accommodate a range of tertiary, secondary, and primary carboxylic acids, as well as exhibit wide functional group compatibility. The chemistry features a high degree of practicality, is scalable, and allows late-stage modification of bioactive pharmaceuticals.

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“…Compared with disulfenylation, thiosulfonylation and disulfonylation, the sulfinysulfonylation of unsaturated bonds is less investigated. The utilization of sulfinyl radicals 145 in synthetic chemistry is relatively limited compared with the well-established sulfonyl and thiyl radical-participated reactions. This might be attributed to the inherent characteristics of sulfinyl radicals, which tend to undergo homodimerization to form thiosulfonates, or engage in reversible additions to π-systems via β-elimination of the sulfinyl group (Scheme 116).…”

Section: Sulfinylsulfonylationmentioning

confidence: 99%