LiBr-Promoted Reaction of β-Ketodithioesters and Thioamides with Sulfoxonium Ylides to Synthesize Functionalized Thiophenes DOI
Subhasish Ray, Neetu Gupta, Maya Shankar Singh

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9401 - 9406

Published: Oct. 22, 2024

An operationally simple and highly efficient synthesis of functionalized thiophenes has been developed by LiBr promoted heteroannulation β-ketodithioesters thioamides with bench-stable sulfoxonium ylides in open air for the first time. This one-pot strategy involves formal Csp3–H bond insertion/intramolecular cyclization cascade, featuring readily accessible starting materials, TM additive-free condition, broad substrate scope, high functional group compatibility, scalability. Moreover, carbonyl, thiomethyl, amino groups resulting thiophene provide a good handle on downstream transformations.

Language: Английский

Perhaloacylation of α-Carbonyl Sulfoxonium Ylides DOI
Varun Anand, Namrata Rastogi

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

Published: Feb. 2, 2025

A mild and efficient protocol for the perhaloacylation of α-carbonyl sulfoxonium ylides has been developed. The commercially available perfluoro- perchloroacid anhydrides were used as acylating agents in catalyst- additive-free reactions to access α-carbonyl-α'-perhaloacyl high yields. reaction offers a simple method prepare valuable polyfluorinated organosulfur molecules.

Language: Английский

Citations

0
Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I(III)/S(VI) Ylides DOI
Shang‐Shi Zhang,

Jiaohang Wei,

Qiong Hu

et al.

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

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
Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans DOI Open Access
Jagadeesh Kalepu, Bapurao Sudam Lad, Pratap Kumar Mandal

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 23, 2024

A new approach for the synthetically important γ-functionalized enals has been developed. The strategy involves rhodium-catalyzed direct C-C & C-S bond forming site-selective γ-difunctionalization of diazoenals with aryl propargyl sulfides via sulfur ylide [2,3] sigmatropic rearrangement, resulting in highly functionalized γ-allenyl(sulfanyl)enals excellent yield at ambient temperature. This versatile constitutes a viable alternative to remote carbonyl-directed γ-functionalization unmodified which suffer from competitive side reactions. synthetic utility was demonstrated by InCl

Language: Английский

Citations

1
Reactions with sulfoxonium ylides using metal-catalysis DOI
Marcio Hayashi, Viktor Saraiva Câmara,

Cristhian S. Oliveira

et al.

Advances in organometallic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 227 - 286

Published: Jan. 1, 2024

Language: Английский

Citations

0
LiBr-Promoted Reaction of β-Ketodithioesters and Thioamides with Sulfoxonium Ylides to Synthesize Functionalized Thiophenes DOI
Subhasish Ray, Neetu Gupta, Maya Shankar Singh

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9401 - 9406

Published: Oct. 22, 2024

An operationally simple and highly efficient synthesis of functionalized thiophenes has been developed by LiBr promoted heteroannulation β-ketodithioesters thioamides with bench-stable sulfoxonium ylides in open air for the first time. This one-pot strategy involves formal Csp3–H bond insertion/intramolecular cyclization cascade, featuring readily accessible starting materials, TM additive-free condition, broad substrate scope, high functional group compatibility, scalability. Moreover, carbonyl, thiomethyl, amino groups resulting thiophene provide a good handle on downstream transformations.

Language: Английский

Citations

0