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

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
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
Generation of Sulfamoyl Radicals via Visible‐Light Mediated Fixation of Sulfur Dioxide for the Synthesis of Sulfonamides DOI Creative Commons
Thais R. Arroio,

Jan Philipp Nau,

Kamil Hofman

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 19, 2024

Abstract Herein, we report a new approach for the light‐mediated generation of sulfamoyl radicals using sulfur dioxide as key building block and direct application these in synthesis sulfonamides. In presence different photoredox catalysts, can be generated directly from SO 2 or surrogate DABSO (1,4‐diazabicyclo[2.2.2]octane⋅bis (sulfur dioxide) adduct) N ‐aminopyridinium salts nitrogen radical precursors. Trapping situ with selected electron‐rich olefins affords sulfonamides up to 86% yield three‐component procedure. This transformation provides complementary synthetic intermediates assembly sulfonamide functionality, privileged motif active pharmaceutical ingredients.

Language: Английский

Citations

0
Visible-Light-Induced Radical Carbon Oximation of Styrenes Using N-Nitrosoamine and Organic Halides DOI

Jinping Lan,

Xiaolong Li, Mengyu Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

An efficient visible-light-induced radical carbon oximation of styrenes with 1-nitrosopyrrolidine and organic halides is developed. The reaction proceeds smoothly in the absence a transition metal photocatalyst under mild conditions, producing wide range functionalized oximes moderate to good yields. Mechanistic studies reveal that involves generation nucleophilic α-amino alkyl radicals subsequent halogen atom transfer (XAT) halides.

Language: Английский

Citations

0
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

0