A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(11), P. 6774 - 6778

Published: Jan. 1, 2024

A novel and attractive photochemical difunctionalization of N -tosyl acrylamide for constructing alkylsulfonylated oxindoles amides with excellent substrate adaptability via a radical Smiles rearrangement strategy is described.

Language: Английский

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

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

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K₂S₂O₈‐Mediated Access to Alkylsulfonated Spiro[4,5] Trienones from N‐Arylpropiolamides with the Insertion of Sulfur Dioxide

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(3), P. 488 - 493

Published: Dec. 23, 2023

Abstract A four‐component reaction of N ‐arylpropiolamides, Hantzsch esters, Na 2 S O 5 and water via a radical cascade cyclization process with the insertion sulfur dioxide mediated by K 8 is reported. series alkylsulfonated spiro[4,5] trienones are prepared up to 86% yield good functional group tolerance substrate applicability. Preliminary mechanism experiments indicate that carbonyl oxygen originated from water.

Language: Английский

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Design of Synthetic Strategies towards Sulfur Containing Scaffolds

Synthesis, Journal Year: 2024, Volume and Issue: 57(02), P. 275 - 295

Published: Aug. 28, 2024

Abstract The utilization of sulfur heterocycles in organic synthesis has attracted significant attention due to their wide-ranging applications. This review showcases the syntheses diverse embedded with amino acid derivatives, polycycles, spirocycles, cyclophanes, and other complex scaffolds. reported methods extend beyond compound highlight use different reagents for constructing heterocycles. Review also discusses utility a variety sulfur-containing starting materials generation target molecules. 1 Introduction 2 Potassium Thioacetate 3 Thiazolidine-2,4-dione 4 Rhodanines 5 Sodium Sulfide 6 Thiotetronic Acid 7 Thiadiazoles 8 Thiophene 9 Rongalite 10 Sulfur Dioxide 11 Divinyl Sulfone 12 Heterocycles Based on Boronic Acids 13 Miscellaneous 14 Summary

Language: Английский

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