Triphasic Hydroxysilylation of Alkenes by Mechanically Piezoelectric Catalysis DOI

Xiaohong Wang,

Xuemei Zhang, X. He

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(49)

Опубликована: Авг. 13, 2024

Abstract The 1,2‐hydroxysilylation of alkenes is crucial for synthesizing organosilicon compounds which are key intermediates in material science, pharmaceuticals, and organic synthesis. development strategies employing hydrogen atom transfer pathways currently hindered by the existence various competing reactions. Herein, we reported a novel mechanochemical strategy triphasic through single‐electron‐transfer pathway. Our approach not only circumvents competitive reactions to enable first‐ever unactivated but also pioneers research mechanic force‐induced under ambient conditions. This gentle method offers excellent compatibility with functional groups, operates simple solvent‐free conditions, ensures rapid reaction time. Preliminary mechanistic investigations suggest that silylboronate can be transformed silicon radical highly polarized Li 2 TiO 3 particles oxygen ball‐milling condition.

Язык: Английский

Triphasic Hydroxysilylation of Alkenes by Mechanically Piezoelectric Catalysis DOI
Xiaohong Wang, Xuemei Zhang, X. He

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(49)

Опубликована: Авг. 13, 2024

Abstract The 1,2‐hydroxysilylation of alkenes is crucial for synthesizing organosilicon compounds which are key intermediates in material science, pharmaceuticals, and organic synthesis. development strategies employing hydrogen atom transfer pathways currently hindered by the existence various competing reactions. Herein, we reported a novel mechanochemical strategy triphasic through single‐electron‐transfer pathway. Our approach not only circumvents competitive reactions to enable first‐ever unactivated but also pioneers research mechanic force‐induced under ambient conditions. This gentle method offers excellent compatibility with functional groups, operates simple solvent‐free conditions, ensures rapid reaction time. Preliminary mechanistic investigations suggest that silylboronate can be transformed silicon radical highly polarized Li 2 TiO 3 particles oxygen ball‐milling condition.

Язык: Английский

Процитировано

6

Merging Iron-Mediated Radical Ligand Transfer (RLT) Catalysis and Mechanochemistry for Facile Dihalogenation of Alkenes DOI
Subrata Patra,

Vasiliki Valsamidou,

Bhargav N. Nandasana

и другие.

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 13747 - 13758

Опубликована: Авг. 30, 2024

With the growing emphasis on cost- and atom-economical chemical synthesis, mechanochemistry has attracted considerable attention for providing environmentally friendly alternatives to traditional solvent-based organic transformations. Herein, we demonstrate use of facilitate alkene dihalogenation via iron-mediated radical ligand transfer (RLT) catalysis, producing diverse vicinal dichloro, dibromo, bromochloro molecules. The method is characterized by its simplicity, rapid reaction time, high chemo- regioselectivity, broad functional group tolerance, accommodating both activated unactivated alkenes alkynes. Mechanistic insights suggest nature these processes, underscoring effectiveness mechanochemically driven RLT catalysis modular functionalization unsaturated hydrocarbons.

Язык: Английский

Процитировано

3

Overcoming High Reduction Potentials via Consecutive Mechanical-Force-Induced Electron Transfer Strategy DOI Creative Commons
Zhong Lian, Xiaohong Wang, X. He

и другие.

Research Square (Research Square), Год журнала: 2025, Номер unknown

Опубликована: Фев. 5, 2025

Abstract Mechanical-force-induced redox catalysis has recently advanced rapidly, emerging as a green and innovative tool in synthetic chemistry. The foundation of this strategy lies the single electron transfer (SET) from polarized piezoelectric materials to substrates, which is initiated by potential generated through mechanical agitation. magnitude primarily influenced intrinsic properties material. In certain circumstances, however, may be insufficient trigger SET process, akin limitations visible-light excitation photocatalytic reactions. This challenge motivated us explore effective solutions. work, we establish catalytic system that utilizes consecutive mechanical-force-induced (ConMET) strategy. novel employs mechanochemical catalysts, with 9-phenyl-dihydroacridine (D1) serving sacrificial donors, facilitating produce significantly more powerful reductive species during grinding. Our approach effectively promotes reduction aryl iodides, bromides even electron-rich chlorides, possess potentials high − 2.8 V (vs. SCE), leading formation radicals. Ultimately, enables anti-Markovnikov hydroarylation alkenes dehalogenative deuteration aromatic halides (Cl, Br) under mild conditions.

Язык: Английский

Процитировано

0

Mechanoredox-Enabled Isothiocyanation of Primary Amines Using Piezoelectric Material as the Redox Catalyst DOI
Miao Wang, Huiying Ren, Shan Jiang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 7, 2025

A novel mechanoredox-enabled synthesis of aromatic and aliphatic isothiocyanates from primary amines carbon disulfide under ball milling conditions using a piezoelectric material (BaTiO3) as the redox catalyst has been developed. This method displays several features, such short reaction time, operational simplicity, room temperature air conditions, minimal solvent, broad substrate scope, recyclable cheap catalyst. Preliminary mechanistic studies revealed that highly polarized acted single-electron transfer (SET) oxidation reagent for key desulfurization process.

Язык: Английский

Процитировано

0

Consecutive mechanical-force-induced electron transfer for reduction of aryl halides with high reduction potentials DOI Creative Commons
Xiaohong Wang, X. He, Xuemei Zhang

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Июнь 4, 2025

Mechanical-force-induced redox catalysis has emerged as a green and expeditous approach in synthetic chemistry, relying on single-electron transfer from polarized piezoelectric materials to substrates initiated by mechanical agitation. However, the potential generated can sometimes be insufficient activate electron process, similar limitations observed photocatalytic reactions. In this work, we introduce catalytic strategy employing consecutive mechanical-force-induced (ConMET) strategy. This uses mechanochemical catalysts with 9-phenyl-dihydroacridine sacrificial donor, enabling efficient transfer. Our method effectively reduces aryl iodides, bromides, even electron-rich chlorides, which possess reduction potentials high -2.8 V (vs. SCE), leading formation of radicals. Ultimately, facilitates anti-Markovnikov hydroarylation alkenes dehalogenative deuteration aromatic halides under mild conditions.

Язык: Английский

Процитировано

0

Mechanochemical Radical Transformations in Organic Synthesis DOI

Jon Sperry,

Sahra Sheikhaleslami

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Окт. 22, 2024

Abstract Organic synthesis has historically relied on solution‐phase, polar transformations to forge new bonds. However, this paradigm is evolving, propelled by the rapid evolution of radical chemistry. Additionally, organic witnessing a simultaneous resurgence in mechanochemistry, formation bonds solid‐state, further contributing shift status quo. The aforementioned advances chemistry have predominantly occurred solution phase, while majority mechanochemical feature transformations. Herein, we discuss rapidly advancing area synthesis: reactions. Solid‐state reactions offer improved green metrics, better reaction outcomes, and access intermediates products that are difficult or impossible reach solution. This review explores these context small molecule synthesis, from early findings current state‐of‐the‐art, underscoring pivotal role solid‐state likely play sustainable chemical synthesis.

Язык: Английский

Процитировано

1

Triphasic Hydroxysilylation of Alkenes by Mechanically Piezoelectric Catalysis DOI

Xiaohong Wang,

Xuemei Zhang, X. He

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(49)

Опубликована: Авг. 13, 2024

Abstract The 1,2‐hydroxysilylation of alkenes is crucial for synthesizing organosilicon compounds which are key intermediates in material science, pharmaceuticals, and organic synthesis. development strategies employing hydrogen atom transfer pathways currently hindered by the existence various competing reactions. Herein, we reported a novel mechanochemical strategy triphasic through single‐electron‐transfer pathway. Our approach not only circumvents competitive reactions to enable first‐ever unactivated but also pioneers research mechanic force‐induced under ambient conditions. This gentle method offers excellent compatibility with functional groups, operates simple solvent‐free conditions, ensures rapid reaction time. Preliminary mechanistic investigations suggest that silylboronate can be transformed silicon radical highly polarized Li 2 TiO 3 particles oxygen ball‐milling condition.

Язык: Английский

Процитировано

0