Construction of α‐ketoamides via Photoredox‐Catalyzed N−H Insertion of Amines by Sulfoxonium Ylides DOI
Xianglin Yu,

Haiyue Yang,

Chang Liu

et al.

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

Published: Nov. 8, 2024

Abstract Herein, we report the development of photoredox‐catalyzed N−H insertion sulfoxonium ylides with amines via oxidative single‐electron transfer (SET). These reactions exhibit broad substrate scope (32 examples) and offer operationally simple, scalable procedures for accessing α ‐ketoamides in a single step. Mechanistic studies control experiments confirm participation photogenerated carbon radical facilitating (SET) from to initiate reaction.

Language: Английский

Visible-Light Photocatalyzed C3–H Alkylation of 2H-Indazoles/Indoles with Sulfoxonium Ylides via Diversified Mechanistic Pathways DOI
Altman Yuzhu Peng, Yujing Wang, Kaifeng Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(2), P. 1193 - 1204

Published: Jan. 9, 2024

Herein, the C3–H alkylation of 2H-indazoles and indoles with sulfoxonium ylides is developed under visible-light photocatalysis. This protocol employs easily accessible reagents, a wide range 2H-indazoles, indoles, are suitable for this reaction to afford desired products benign conditions. Synergistic experimental computational studies suggest that involving photocatalysis could proceed via different mechanistic pathways. For C3-alkylation triplet energy transfer pathway proposed quenching excited photocatalyst. Subsequently, formed state undergo radical attack on C═S moiety ylides. After dissociation DMSO 1,2-H migration, final product be yielded. However, such not applicable indoles. Instead, converted C-centered in presence KH2PO4 photoredox The can C3-site thus lead

Language: Английский

Citations

13

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

Ning Xian,

Xiaochen Ji, Guo‐Jun Deng

et al.

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

Citations

1

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

Ning Xian,

Jiang Yin,

Xiaochen Ji

et al.

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

Citations

9

Metal-free cascade O–H double insertion between I(III)/S(VI)-ylides, carboxylic acids, and alcohols: modular access to unsymmetrical α,α-O,O-substituted ketones DOI

Jiaohang Wei,

Wen‐Xuan Zou,

Qiong Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3234 - 3241

Published: Jan. 1, 2024

Herein, we present a cascade O–H double insertion reaction between I (III) /S (VI) -ylides, carboxylic acids, and alcohols under metal-free conditions, enabling the modular synthesis of unsymmetrical α,α- O , -substituted ketones.

Language: Английский

Citations

8

Copper-Mediated Cyclization of Terminal Alkynes with CF3-Imidoyl Sulfoxonium Ylides To Construct 5-Trifluoromethylpyrroles DOI
Magdy I. El‐Zahar, Zhou Li,

Yixin Tong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2249 - 2254

Published: March 7, 2024

A copper-mediated [3 + 2] cyclization of CF3-imidoyl sulfoxonium ylides and terminal alkynes has been demonstrated. This work provides a practical approach for assembling 5-trifluoromethylpyrroles with the merits broad substrate scope, good functional tolerance, mild reaction conditions. Control experiments DFT studies indicate that this may involve addition π-bonds by copper-carbene radicals hydrogen migration.

Language: Английский

Citations

6

Visible light-promoted [3+2] cyclization reaction of vinyl azides with perfluoroalkyl-substituted-imidoyl sulfoxonium ylides DOI
Ming Yang,

Yuxuan Meng,

Haroon Mehfooz

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(41), P. 5407 - 5410

Published: Jan. 1, 2024

A visible-light-induced [3+2] cyclization of vinyl azides with perfluoroalkyl-substituted imidoyl sulfoxonium ylides has been developed and provides a new efficient method for the construction 1-pyrrolines.

Language: Английский

Citations

6

Photochemical Reactions of Sulfur Ylides DOI
Radell Echemendía,

Kauê C. Capellaro,

Antonio C. B. Burtoloso

et al.

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(13), P. 978 - 990

Published: May 6, 2024

Abstract: Photochemical reactions offer unparalleled opportunities to access elusive chemical pathways and develop innovative strategies for constructing complex molecules. Within organic synthesis, photochemical have become indispensable tools accessing molecular structures, such as pharmaceuticals natural products. The ability of sulfur ylides participate in these diverse processes has made them the synthetic chemist's toolbox. use transformations garnered significant attention chemistry community, they serve powerful intermediates several transformations. This review article presents a comprehensive overview mediated by ylides. Herein, we describe key aspects reactivity presence light. compounds can be classified into three categories: energy acceptors, electron donors, trapping reagents.

Language: Английский

Citations

4

Unprecedented Dual Radical Initiation in Visible-Light Photoredox-Catalyzed X–H (X = Si and B) Insertions of Sulfoxonium Ylides DOI

Mengyu Xu,

Yujing Wang, Rui Fu

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7003 - 7014

Published: April 15, 2025

Language: Английский

Citations

0

Divergent Synthesis of Dihydrofuran and Dienol Scaffolds via Pd-Catalyzed Decarboxylative Carbene Cross-Coupling DOI
Xiaolong Ma,

Erfei Miao,

Yili Sun

et al.

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

Published: April 24, 2025

Herein, we report a novel ligand-switchable Pd-catalyzed carbene coupling reaction employing vinylethylene carbonates and sulfoxonium ylides. By proper choice of ligands, the chemoselectivity process could be efficiently regulated, allowing for availability dihydrofuran or dienol scaffolds. This method features mild conditions, broad scope, remarkable synthetic utility. Compound 6f can effectively stimulate secretion GLP-1, providing promising insight into development small-molecule agonists GLP-1 receptor.

Language: Английский

Citations

0

Lithium Bromide-Promoted Formal C(sp3)–H Bond Insertion Reactions of β-Carbonyl Esters with Sulfoxonium Ylides to Synthesize 1,4-Dicarbonyl Compounds DOI

Hailin Guo,

Yuhao Ding,

Jingwen Fan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 6974 - 6986

Published: May 4, 2024

A LiBr-promoted formal C(sp3)–H bond insertion reaction between β-carbonyl esters and sulfoxonium ylides is established. This practical has a wide range of substrate scope for both to give variety 1,4-dicarbonyl compounds with 43–94% yields. The features transition-metal-free conditions exclusive C-alkylation chemselectivity. use bench-stable overcomes previous methods that require transition metal as catalysts unstable diazo or toxic haloketones alkylation reagents.

Language: Английский

Citations

2