Photocatalytic Sulfonyl Peroxidation of Alkenes via Deamination of <i>N</i>-Sulfonyl Ketimines

Feng, Yuting; Chen, Shujun; Lv, Leiyang; Yaremenko, Ivan A.; Terent’ev, Alexander O.; Li, Zhiping

doi:10.1021/acs.orglett.4c00241

Cited by 5 publications

(1 citation statement)

References 47 publications

(28 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2024, Li and co-workers reported in similar approach the peroxysulfonilation of vinyl bonds with sulfonylimines and tertbutylperoxide. [56] The mechanism relies on the EnT of OPC-3 to the sulfoximine, generating the sulfonyl radical which adds to the double bond. The so generated benzylic radical is trapped with tert-butylperoxide to yield the corresponding peroxide, which could be further derivatized into hydroxyl and keto derivatives.…”

Section: Activation Of Sulfonamides Via Sulfonyliminesmentioning

confidence: 99%

Photocatalytic Synthesis and Functionalization of Sulfones, Sulfonamides and Sulfoximines

Garrido‐González,

Medrano‐Uribe,

Rosso

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

Sulfur(VI)‐based functional groups are popular scaffolds in a wide variety of research fields including synthetic and medicinal chemistry, as well as chemical biology. The growing interest in sulfur(VI)‐containing molecules has motivated the scientific community to explore new methods to synthesize and modify them. Here, photocatalysis plays a key role granting access to new types of reactivity under mild reaction conditions. In this Perspective, we present a selection of works reported in the last six years focused on the photocatalytic assembly and reactivity of sulfones, sulfonamides, and sulfoximines. We addressed the key synthetic intermediates for each transformation, while discussing limitations and strength points of the protocols. Future directions of the field are finally presented.

show abstract

Section: Activation Of Sulfonamides Via Sulfonyliminesmentioning

confidence: 99%

Photocatalytic Synthesis and Functionalization of Sulfones, Sulfonamides and Sulfoximines

Garrido‐González,

Medrano‐Uribe,

Rosso

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

show abstract

Photo‐Induced Sulfonylation/Trifluoromethylation‐Peroxidation of Alkenes via EnT‐Mediated N−S Bond Homolysis of N‐Sulfonyl Ketimines

Feng,

Lv,

2024

Asian J Org Chem

View full text Add to dashboard Cite

Photocatalytic sulfonylation/trifluoromethylation‐peroxidation of alkenes with N‐sulfonyl ketimines and tert‐butyl hydroperoxide is reported. The transformation is initiated by the EnT‐driven homolytic S−N bond cleavage of N‐sulfonyl ketimines. The sulfonyl‐peroxides were obtained when alkyl sulfonyl radicals were captured by alkene via sequential C−S and C−O bond formation, while a thermodynamically favored release of SO2 from trifluoromethane sulfonyl radical generated CF3 radical and afforded the trifluoromethyl‐peroxides.

show abstract

Visible-light-induced Synthesis of Organic Peroxides via Decarboxylative Couplings of Carboxylic Acids, Alkenes and tert-Butyl Hydroperoxide

Huang,

Lou,

et al. 2024

Chem. Res. Chin. Univ.

View full text Add to dashboard Cite

Photocatalytic Sulfonyl Peroxidation of Alkenes via Deamination of N-Sulfonyl Ketimines

Abstract: Published as part of Organic Letters virtual special issue "Radical Reactions for the Construction and Transformation of Complex Molecules".

Cited by 5 publications

References 47 publications

Photocatalytic Synthesis and Functionalization of Sulfones, Sulfonamides and Sulfoximines

Photocatalytic Synthesis and Functionalization of Sulfones, Sulfonamides and Sulfoximines

Photo‐Induced Sulfonylation/Trifluoromethylation‐Peroxidation of Alkenes via EnT‐Mediated N−S Bond Homolysis of N‐Sulfonyl Ketimines

Visible-light-induced Synthesis of Organic Peroxides via Decarboxylative Couplings of Carboxylic Acids, Alkenes and tert-Butyl Hydroperoxide

Contact Info

Product

Resources

About