Visible Light-Driven Interrupted Barton Reaction: Intermolecular Radical-Relay Sulfonyloximation of Alkenes with DABSO and Alkyl Nitrites DOI
Wei Li, Li Zhao,

Chenchen Diao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 24, 2024

A visible light-driven, intermolecular interrupted Barton reaction has been developed for radical-relay sulfonyloximation of alkenes with alkyl nitrites, using DABSO as a trapping reagent. This method overcomes the challenges competing normal reactions and polarity mismatches by rapidly irreversibly capturing radicals, preventing unwanted side reactions. The resulting polarity-reversed sulfonyl radicals undergo highly selective addition to alkenes, yielding α-alkylsulfonyl ketoximes tethered hydroxyl or ketone groups. Conducted under mild light conditions, this approach eliminates need harsh mercury lamps, offering scalable, chemoselective synthesizing valuable sulfonylated oxime derivatives.

Language: Английский

Photoinduced Vicinal Sulfamoyloximation of Alkenes: Harnessing Bifunctional Nitrosamines via a Rapid Radical Trapping Strategy DOI
Wei Li,

Chenchen Diao,

Yilian Lu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6253 - 6258

Published: July 17, 2024

We developed a photoinduced method for vicinal sulfamoyloximation of alkenes using

Language: Английский

Citations

7
Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent DOI
Huihui Yang, Miaomiao Li, Aijun Zhang

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110425 - 110425

Published: Oct. 1, 2024

Language: Английский

Citations

3
C(sp3)—H Bond Oximinylation DOI

Antuo Xu,

Junyi Li, Qiang Liu

et al.

Acta Chimica Sinica, Journal Year: 2025, Volume and Issue: 83(4), P. 390 - 390

Published: Jan. 1, 2025

Language: Английский

Citations

0
Photosensitized Imino-Sulfamoylation of Alkenes with Oxime Carbamates DOI

Ai-Lian Wang,

Huan-Huan Zhao,

Haowen Jiang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

In this study, we have devised a strategy that employs oxime carbamate as bifunctional diamination reagent in combination with SO2 to realize imino-sulfamoylation of alkenes. This protocol is characterized by its mild conditions, operational simplicity, and metal-free nature, while demonstrating broad functional group tolerance for Furthermore, the application method provides an accessible route diverse range β-amino sulfonamide derivatives.

Language: Английский

Citations

0
Direct vicinal sulfonyloximation of alkenes: an efficient and straightforward approach towards the synthesis of α-sulfonyl ketoximes DOI Creative Commons
Zinatossadat Hossaini, Shahrzad Abdolmohammadi,

Shakir Mahmood Saeed

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(22), P. 17174 - 17185

Published: Jan. 1, 2025

Direct vicinal sulfonylative difunctionalization of simple alkenes represents a powerful strategy for the rapid assembly β-functionalized sulfones from starting materials.

Language: Английский

Citations

0
Reactivity Tuning for Selective Aldimino-Sulfonylation of Styrenes by Photocatalytic Activation of Sulfonyl Aldimines DOI

Jia Huang,

Nuerzhati Nuermaimaiti,

Qiuping Ding

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 31, 2025

Imino-sulfonylation of styrene represents a powerful method for constructing highly functionalized molecules, while only diphenyl imines were able to be employed in previous reports. By modulating the electron property styrene, visible-light-mediated radical/radical cross-coupling aldiminyl radical and carbon-centered was achieved synthesize diverse aldimine-embedded sulfones by using sulfonyl aldimines α-trifluoromethylstyrenes. One-pot oxidation delivered Ritter-type amidation products without need excessive nitriles as solvent. Furthermore, this protocol took advantage simple reaction conditions, good substituent diversity, high atom economy broaden research radicals amination alkenes.

Language: Английский

Citations

0
DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

Citations

2
Visible Light-Driven Interrupted Barton Reaction: Intermolecular Radical-Relay Sulfonyloximation of Alkenes with DABSO and Alkyl Nitrites DOI
Wei Li, Li Zhao,

Chenchen Diao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 24, 2024

A visible light-driven, intermolecular interrupted Barton reaction has been developed for radical-relay sulfonyloximation of alkenes with alkyl nitrites, using DABSO as a trapping reagent. This method overcomes the challenges competing normal reactions and polarity mismatches by rapidly irreversibly capturing radicals, preventing unwanted side reactions. The resulting polarity-reversed sulfonyl radicals undergo highly selective addition to alkenes, yielding α-alkylsulfonyl ketoximes tethered hydroxyl or ketone groups. Conducted under mild light conditions, this approach eliminates need harsh mercury lamps, offering scalable, chemoselective synthesizing valuable sulfonylated oxime derivatives.

Language: Английский

Citations

1