Visible Light Driven α-Sulfonylation of Ketone-Derived Silyl Enol Ethers via Electron Donor-Acceptor Complex DOI Creative Commons

Barakha Saxena,

Roshan I. Patel,

Anuj Sharma

и другие.

Опубликована: Авг. 27, 2024

The diverse utility of β-ketosulfones in pharmaceuticals and bioactive compounds has generated considerable interest their synthesis. However, existing synthetic approaches often depend on transition-metal catalysts, which require extensive purification low yields. Herein, we present a cost-effective, metal-, photocatalyst-free, visible light electron donor-acceptor (EDA) complex-mediated sulfonylation ketone-derived silyl enol ethers with thiosulfonates (acceptor) DABCO as an donor under mild conditions, offering more efficient straightforward approach. Our method enables the synthesis range β-keto sulfone derivatives, including biologically active late-stage molecules, good strategy offers several significant advantages over techniques, include (i) photoredox catalyst-free; (ii) external SO2-source-free; (iii) broad substrate scope; (iv) recyclable reusable by-product; (v) excellent atom economy, reaction mass efficiency, process intensity, E-factor EcoScale scores, highlighting its efficiency economic sustainability. Detailed mechanistic studies confirm involvement EDA-complex mediated radical that operates without catalyst.

Язык: Английский

Recent Natural Product Total Syntheses Involving Cycloadditions of Allenes DOI Open Access

Chen‐Chen Gu,

Xi Long, Xiuping Chen

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 11, 2025

Comprehensive Summary Allenes, characterized by their cumulated carbon–carbon double bonds, have emerged as indispensable synthons in the construction of complex natural products. Their unique reactivity and stereochemical properties render allenes a powerful tool for efficient streamlined total synthesis structurally intricate This review comprehensively summarizes syntheses products involving allene cycloaddition reactions reported over past decade (2014—2024). Among nearly 20 reviewed, [2+1], [2+2], [3+2], [4+2], [4+3], [5+1] [2+2+1] are most important transformations to construct key skeleton. is because ability form multiple bonds single step with high atom economy, stereoselectivity, regioselectivity, often under mild conditions. The strategic application these forming controlling stereochemistry makes them practical assembly molecular frameworks. With ongoing exploration methods generation, particularly enantioselective approaches, continued discovery novel cyclization allenes, chemistry will maintain its crucial role Key Scientists

Язык: Английский

Процитировано

0
Nickel-Catalyzed Reductive 1,4-Alkylacylation of 1,3-Enynes Enabling Synthesis of Allenyl Ketones DOI

Quanyuan Wang,

Keyi Peng,

Xupei Yao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

A nickel-catalyzed reductive 1,4-alkylacylation of 1,3-enynes has been established using nonactivated tertiary alkyl bromides and aromatic anhydrides as dual electrophiles. This protocol enables efficient assembly tetrasubstituted allenyl ketones with high chemo- regioselectivity. Mechanistic insights reveal the radical relay process involving synergistic interactions nickel zinc. The ketone products serve modular building blocks, particularly for constructing fully carbon-substituted furans via Au-catalyzed cycloisomerization selective 1,2-aryl migration, enhancing synthetic practicality.

Язык: Английский

Процитировано

0
Visible Light Driven α-Sulfonylation of Ketone-Derived Silyl Enol Ethers via Electron Donor-Acceptor Complex DOI Creative Commons

Barakha Saxena,

Roshan I. Patel,

Anuj Sharma

и другие.

Опубликована: Авг. 27, 2024

The diverse utility of β-ketosulfones in pharmaceuticals and bioactive compounds has generated considerable interest their synthesis. However, existing synthetic approaches often depend on transition-metal catalysts, which require extensive purification low yields. Herein, we present a cost-effective, metal-, photocatalyst-free, visible light electron donor-acceptor (EDA) complex-mediated sulfonylation ketone-derived silyl enol ethers with thiosulfonates (acceptor) DABCO as an donor under mild conditions, offering more efficient straightforward approach. Our method enables the synthesis range β-keto sulfone derivatives, including biologically active late-stage molecules, good strategy offers several significant advantages over techniques, include (i) photoredox catalyst-free; (ii) external SO2-source-free; (iii) broad substrate scope; (iv) recyclable reusable by-product; (v) excellent atom economy, reaction mass efficiency, process intensity, E-factor EcoScale scores, highlighting its efficiency economic sustainability. Detailed mechanistic studies confirm involvement EDA-complex mediated radical that operates without catalyst.

Язык: Английский

Процитировано

1