Mechanochemical Synthesis of Aryl Fluorides by Using Ball Milling and a Piezoelectric Material as the Redox Catalyst DOI
Xiaohong Wang, Xuemei Zhang, Xue Li

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(39)

Published: July 31, 2023

Abstract Aryl fluorides are important structural motifs in many pharmaceuticals. Although the Balz–Schiemann reaction provides an entry to aryl from aryldiazonium tetrafluoroborates, it suffers drawbacks such as long time, high temperature, toxic solvent, gas release, and low functional group tolerance. Here, we describe a general method for synthesis of tetrafluoroborates using piezoelectric material redox catalyst under ball milling conditions presence Selectfluor. This approach effectively addresses aforementioned limitations. Furthermore, can be recycled multiple times. Mechanistic investigations indicate that this fluorination may proceed via radical pathway, Selectfluor plays dual role both source fluorine terminal reductant.

Language: Английский

A Review on Piezoelectric-mediated Mechanoredox Reactions by Ball Milling in Organic Synthesis DOI
Shan Jiang, Miao Wang

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(12), P. 905 - 913

Published: May 6, 2024

Abstract: Recently, the concept of mechanoredox chemistry has been proposed and welldeveloped in organic synthesis. Mechanoredox is conceptually similar to a photocatalyst reaction system, where piezoelectric materials are introduced system manner analogous photoredox catalysis. These reactions feature ability generate high-value radicals that do not require harsh conditions anhydrous anaerobic conditions, an expensive photocatalyst, use solvents, which renders these transformations highly industrially applicable. In addition, also emerging interdisciplinary research field combines material with synthetic create more useful reactions. This review provides comprehensive summary progress date specific transformation related mechanisms piezoelectric- mediated by ball milling

Language: Английский

Citations

4
Redox Reactions of Organic Molecules Using Rotating Magnetic Field and Metal Rods DOI
Haodong Liu,

Xuliang Han,

Xiaomei Feng

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(26), P. 18143 - 18150

Published: June 25, 2024

In recent years, redox reactions have harnessed light or mechanical energy to enable the formation of chemical bonds. We postulated a complementary approach that electromagnetic induction could promote reaction organic molecules using rotating magnetic field and metal rods. Here, we report electromotive force activates redox-active trifluoromethylating reagents. This magnetoredox system can be applied trifluoromethylation heteroarenes with high regioselectivity hydrotrifluoromethylation alkenes without need for catalysts additives.

Language: Английский

Citations

4
Ball mill-induced piezocatalysis assessment for dye degradation using BiVO4 DOI

Manish Kumar,

Imen Kebaïli, Rahul Vaish

et al.

Materials Today Communications, Journal Year: 2023, Volume and Issue: 37, P. 107306 - 107306

Published: Oct. 11, 2023

Language: Английский

Citations

10
Ball milling assisted mechano-catalytic dye degradation using SrTiO3 nanoparticles DOI Creative Commons
Aman Shukla, Akshay Gaur,

Shivam Dubey

et al.

RSC Mechanochemistry, Journal Year: 2024, Volume and Issue: 1(5), P. 465 - 476

Published: Jan. 1, 2024

Ball milling, traditionally employed for the synthesis of nanomaterials, have now been utilized as a direct driver catalysis due to its capability surface charge separation.

Language: Английский

Citations

3
Mechanoredox‐Catalyzed Organic Synthesis with Piezoelectric Materials: Quo Vadis? DOI Open Access
Hanggara Sudrajat, Hsien‐Yi Hsu, François Jérôme

et al.

ChemCatChem, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 24, 2025

Abstract Piezoelectric materials offer great promise due to their ability generate electric fields under mechanical stress, producing surface charges that drive otherwise kinetically sluggish redox reactions. The strained surfaces of these provide a unique advantage in controlling product selectivity and enabling reaction pathways are unattainable with conventional methods. This perspective highlights advancements, challenges, the future potential piezoelectric synthetic organic chemistry, focus on designing optimized for piezocatalyzed synthesis. Piezocatalysis is industrially relevant because its operational simplicity, mild, gram scale synthesis reusable catalysts, minimal solvent use, air tolerant conditions. It involves cycles facilitate one electron events without requiring light exposure or electrical bias. Despite significant progress, many fundamental aspects yet be fully understood. One example correlation between piezoelectricity catalytic activity, which not always linear, as demonstrated by comparison tetragonal cubic BaTiO₃. While BaTiO₃ piezoelectric, it shows excellent activity certain reactions such arylation, dicarbonylation, cyclization mechanochemical conditions comparable Considering all aspects, this aims stimulate discussion advance promising field right direction.

Language: Английский

Citations

0
Overcoming High Reduction Potentials via Consecutive Mechanical-Force-Induced Electron Transfer Strategy DOI Creative Commons
Zhong Lian, Xiaohong Wang, X. He

et al.

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 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.

Language: Английский

Citations

0
Mechanoredox-Enabled Isothiocyanation of Primary Amines Using Piezoelectric Material as the Redox Catalyst DOI
Miao Wang, Huiying Ren, Shan Jiang

et al.

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

Published: Feb. 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.

Language: Английский

Citations

0
Ball‐Milling‐Promoted Copper‐Catalyzed Solid‐State Radical C–H Difluoroalkylation Reactions DOI Creative Commons
Ran Zhang, Chung‐Bang Yun, Hong Lu

et al.

ChemistryEurope, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

A mechanochemical strategy for promoting copper‐catalyzed solid‐state radical C–H difluoroalkylation reactions has been devised. Compared to traditional solution‐based methods, this mechanoredox approach offers enhanced ease of handling, greater cleanliness, and improved sustainability the synthesis difluoroalkylated indoles, which constitute crucial structural motifs in contemporary drug discovery. The underlying reaction mechanism is investigated through meticulous step‐by‐step control experiments that highlighted substantial influence conditions. versatility protocol demonstrated by its applications complex natural products derivatives.

Language: Английский

Citations

0
Enhancing Piezo-Catalytic Hydrogen Evolution on BiOCl through UV Irradiation DOI

Fan Su,

Junying Nie,

Hongbo Yu

et al.

Inorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 29, 2025

Hydrogen production from water using piezo-catalysis is increasingly popular, but it typically requires expensive noble metal cocatalysts to speed up the reactions. In this study, we found that a UV irradiation treatment on piezoelectric material BiOCl enhances its H2 evolution by 6.8 folds, 0.41 2.81 mmol/g/h, even outperforming those loaded with cocatalysts. Our experiments and simulations revealed prompts in situ reduction of lattice Bi3+ BiOCl, creating Bi nanoparticles surface. These serve as cocatalysts, enhancing hydrogen (1) capturing piezo-generated electrons Bi's higher work function; (2) facilitating charge transfer between due their intimate contact; (3) improving kinetics more suitable H* adsorption strength. This UV-enhancement technique can be applied various Bi-based materials (e.g., BiOBr, BiOI, Bi2WO6, etc.) well piezo-catalytic dye degradation reactions, demonstrating versatility potential for broader applications. research provides straightforward cost-effective approach improve performance without need costly

Language: Английский

Citations

0
Synthesis of Nonclassical Heteroaryl C-Glycosides via Decarboxylative C–H Glycosylation DOI
Cuimei Zhang,

Dongqin He,

Zhaohui Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10112 - 10126

Published: July 3, 2024

A photoredox-promoted decarboxylative C-H glycosylation for the synthesis of nonclassical heteroaryl C-glycosides is reported. This methodology characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. Moreover, operational procedure simple, gram-scale highlights practical applicability this protocol.

Language: Английский

Citations

3