A ruthenium catalyzed Dolye–Kirmse rearrangement reaction of sulfoxonium ylides with sulfides or selenides

Hao, Yingdi; Ji, Liang; Lin, Zhiqian; Huang, Tianle; Xu, Ya-Di; Guo, Li; Yang, Zhongzhen; Wu, Yong

doi:10.1039/d3qo00706e

Cited by 5 publications

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans

Kalepu,

Sudam Lad,

Kumar Mandal

et al. 2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

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 the highly functionalized γ−allenyl(sulfanyl)enals in excellent yield at ambient temperature. This highly versatile approach constitutes a viable alternative to the remote carbonyl‐directed γ−functionalization of unmodified enals which suffer from competitive side reactions. The synthetic utility of the γ−allenyl(sulfanyl)enals was demonstrated by the InCl3‐catalyzed cycloisomerization to the trisubstituted furanyl‐enals via an unusual 1,4‐sulfanyl migration. In addition, an operationally simple and efficient one‐pot [3+2] annulation of diazoenals and propargyl sulfides, involving combined γ−difunctionalization and cycloisomerization was successfully developed for the diverse enal‐functionalized furans.

show abstract

Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans

Kalepu,

Sudam Lad,

Kumar Mandal

et al. 2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

Reactions with sulfoxonium ylides using metal-catalysis

Hayashi,

Câmara,

Oliveira

et al. 2024

Advances in Organometallic Chemistry

View full text Add to dashboard Cite

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

Guo,

Ding,

Fan

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

A LiBr-promoted formal C(sp 3 )−H bond insertion reaction between β-carbonyl esters and sulfoxonium ylides is established. This practical reaction has a wide range of substrate scope for both β-carbonyl esters and sulfoxonium ylides to give a variety of 1,4-dicarbonyl compounds with 43−94% yields. The reaction features transition-metal-free reaction conditions and exclusive C-alkylation chemselectivity. The use of bench-stable sulfoxonium ylides overcomes previous methods that require transition metal as catalysts and unstable diazo compounds or toxic haloketones as alkylation reagents.

show abstract

A ruthenium catalyzed Dolye–Kirmse rearrangement reaction of sulfoxonium ylides with sulfides or selenides

Abstract: Ruthenium-catalyzed Dolye-Kirmse rearrangement reaction of sulfoxonium ylides to afford sulfide or selenide-containing compounds has been developed. Sulfoxonium ylides as safe and stable starting materials were used in the Dolye-Kirmse rearrangement...

Cited by 5 publications

References 50 publications

Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans

Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans

Reactions with sulfoxonium ylides using metal-catalysis

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

Contact Info

Product

Resources

About

A ruthenium catalyzed Dolye–Kirmse rearrangement reaction of sulfoxonium ylides with sulfides or selenides

Abstract: Ruthenium-catalyzed Dolye-Kirmse rearrangement reaction of sulfoxonium ylides to afford sulfide or selenide-containing compounds has been developed. Sulfoxonium ylides as safe and stable starting materials were used in the Dolye-Kirmse rearrangement...

Cited by 5 publications

References 50 publications

Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans

Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans

Reactions with sulfoxonium ylides using metal-catalysis

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

Contact Info

Product

Resources

About

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