Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes

Tetrahedron, Journal Year: 2025, Volume and Issue: 173, P. 134467 - 134467

Published: Jan. 12, 2025

Language: Английский

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Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4972 - 5027

Published: Jan. 1, 2023

This review comprehensively summarizes the dichalcogenative functionalization of unsaturated compounds over past decade. The scopes, limitations and detailed reaction mechanisms are also discussed.

Language: Английский

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Recent Advances in Electrochemical Sulfonylation using Sodium Sulfinates as Sulfonyl Radical Precursors

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(2), P. 105 - 116

Published: Jan. 1, 2024

Abstract: Sodium sulfinates have been widely utilized as sulfonyl radical precursors for preparing a diverse array of value-added sulfur-containing compounds (sulfones, sulfonamides, sulfonates, thiosulfonates, etc.) through S-C, S-N, S-O and S-S bonds formation reactions. Organic electrosynthesis has become an attractive alternative to conventional methods redox reactions because it utilizes electric current instead chemical agents. As such, the electrochemical generation radicals from sodium their applications in organic attracted much attention. In this review, recent advances sulfonylation involving since 2015 were reviewed, along with related reaction mechanisms.

Language: Английский

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The Strategies towards Electrochemical Generation of Aryl Radicals

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 16, 2024

The advancement in electrochemical techniques has unlocked a new path for achieving unprecedented oxidations and reductions of aryl radical precursors controlled selective manner. This approach facilitates the construction aromatic carbon-carbon carbon-heteroatom bonds. In light green merits growing importance this technique chemistry, review aims to provide an overview recent advance generation radicals organized by precursor type, with focus on substrate scope, limitation, underlying mechanism, thereby inspiring future work generation.

Language: Английский

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Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10660 - 10677

Published: July 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Language: Английский

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Electrochemical Oxidative Annulation of Inactivated Alkynes for the Synthesis of Sulfonated 2H-Chromene Derivatives

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2793 - 2797

Published: April 18, 2023

A unique, facile, and straightforward electrochemical oxidative annulation of inactivated propargyl aryl ethers with sulfonyl hydrazides leading to 3-sulfonated 2H-chromenes has been achieved. Significantly, this protocol involves a green approach that works under mild reaction conditions using constant current in an undivided cell is devoid oxidants catalysts. Notably, the process exhibited broad scope functional group tolerance deliver would represent alternative sustainable strategy versus conventional chromene synthesis.

Language: Английский

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Radical bicyclization of 1,6-enynes with sulfonyl hydrazides by the use of TBAI/TBHP in the aqueous phase

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(42), P. 6391 - 6394

Published: Jan. 1, 2023

A novel 5-exo-dig/6-endo-trig bicyclization of 1,6-enynes with sulfonyl hydrazides in the aqueous phase using cheap and available tetrabutylammonium iodide (TBAI)-tert-butyl hydroperoxide (TBHP) combined system is reported. The resulting reaction diverse nitrogen- oxygen-polyheterocycles displays high chemical selectivity, step-economy, a moderate substrate scope. Moreover, iodosulfonylation can be realized by modulating structure 1,6-enynes.

Language: Английский

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Photoredox-Catalyzed Radical–Radical Cross-Coupling of Sulfonyl Chlorides with Trifluoroborate Salts

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 11161 - 11172

Published: July 25, 2023

Sulfones are widely found in natural products and drug molecules. Here, we disclose a strategy for direct synthesis of sulfone compounds with diverse structures by visible-light-catalyzed radical-radical cross-coupling sulfonyl chlorides trifluoroborate salts. Allyl, benzyl, vinyl, aryl trifluoroborates can be successfully cross-coupled (hetero)aryl alkyl chlorides, respectively. This features redox neutrality, good substrate generality, simple operation, benign reaction conditions.

Language: Английский

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Controlled Electrochemical C4 Sulfonylation of 1(2H)-isoquinolone derivatives: Through the isomerization of N-radical to C-radical

Tetrahedron, Journal Year: 2025, Volume and Issue: 174, P. 134506 - 134506

Published: Jan. 28, 2025

Language: Английский

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Electrochemical Synthesis of β-Keto Sulfones from Enol Acetates and Sulfonyl Hydrazides

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

Published: March 20, 2025

A novel and environmentally friendly strategy has been developed for the efficient electrochemical synthesis of β-keto sulfones. This method enables sulfones by reacting easily available sulfonylhydrazide with enol acetate under mild conditions, especially without need transition metal catalysts or oxidants, which can achieve high yields. The scope this reaction was systematically explored various sulfonyl hydrazides acetates. scale-up successfully accomplished using an flow cell, demonstrating industrial applicability approach. Moreover, underlying mechanism further investigated through free radical scavenging experiments cyclic voltammetry studies.

Language: Английский

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