A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5811 - 5816

Published: June 28, 2024

A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization hybrid I(III)/S(VI) is presented. This process allows efficient P–H insertion under Cu catalysis, enabling synthesis ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC(S)OR, KSCN mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, thiocyanation accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, various product derivatizations highlight synthetic utility this protocol.

Language: Английский

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Stereoselective Three-Component Carbocyclization of 1,7-Enynes with Sulfoxonium Ylides and Water under Photoredox Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6736 - 6741

Published: July 29, 2024

A visible-light-induced photoredox three-component carbocyclization reaction of 1,7-enynes with sulfoxonium ylides and water is reported. The protocol provides a facile entry to structurally valuable highly functionalized cyclopenta[c]quinoline scaffolds in chemoselective stereoselective manner. Salient features this method include redox-neutral conditions, no requirement base or other additive, good functional-group tolerance.

Language: Английский

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Visible-Light-Induced photoredox aerobic coupling of sulfonium ylides and amines leading to E-selective formation of 2-amino-2-butene-1,4-diones

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel visible-light-induced photoredox three-component aerobic coupling reaction of sulfoxonium ylides and amines is reported.

Language: Английский

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Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I^(III)/S^(VI) Ylides

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

Published: April 1, 2025

The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation I(III)/S(VI) with 1,3-dicarbonyls. By slight modification reaction conditions, controllable alkylation-hydroxylation and dialkylation were achieved. This strategy affords a diverse array α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement sulfoxonium highlight divergent reactivity ylides.

Language: Английский

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Recent Advances on Direct Phosphorothiolation Reactions

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

Published: July 23, 2024

Abstract Organophosphorothioates are organic molecules containing sulfur and phosphorus, with significant biological activity physicochemical properties, widely used in synthesis, medicinal chemistry, the agrochemical industry. In particular, many phosphorothioates display a variety of activities, such as antifungal, antibacterial, anti‐parasite, anticancer, so on. Traditionally, synthesis has mainly relied on indirect methods involving construction S−P bond. recent years, direct phosphorothiolation gained attention reliable rapid method for introducing −S−P(O)(OR) 2 group into parent molecules. This article reviews latest advances reactions, categorized based different sources group.

Language: Английский

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Formation of cyclopenta[c]quinolines through visible-light-induced photoredox cascade bis-annulations of 1,7-enynes with sulfoxonium ylides

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(37), P. 7618 - 7622

Published: Jan. 1, 2024

A novel visible-light-driven photoredox-catalyzed cascade bicyclization of 1,7-enynes with aqueous sulfoxonium ylides is reported. The reaction highly chemoselective three new C-C bonds, two rings, and an all-carbon quaternary stereocenter constructed in a one-pot fashion. This mild protocol features remarkably broad substrate scope good functional group tolerance, providing general practical approach to access various cyclopenta[

Language: Английский

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High-throughput experimentation and machine learning-promoted synthesis of α-phosphoryloxy ketones via Ru-catalyzed P(O)O-H insertion reactions of sulfoxonium ylides

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Language: Английский

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Isocyanide-Based Multicomponent Reaction: Cascade α-Acyloxylation/Carboxamidation and [3 + 1+1] Cyclization of I^(III)/S^(VI)-Ylides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6263 - 6268

Published: July 12, 2024

A metal-free cascade of α-acyloxylation/carboxamidation I(III)/S(VI)-ylides, carboxylic acids, and isonitriles via a Passerini-like multicomponent reaction is reported. Unexpectedly, [3 + 1+1] cyclization involving I(III)/S(VI)-ylides two molecules ethyl isocyanoacetate was observed. The strategy allows for the synthesis unsymmetrical α,α-disubstituted ketones functionalized pyrroles with up to 99% yield wide substrate compatibility. Notably, procedure has been extended late-stage modification drugs natural products, offering an elegant complement classic Passerini reaction.

Language: Английский

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