Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst DOI

Ruiling Qu,

Shan Wan, Xuemei Zhang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(28)

Published: April 30, 2024

Abstract The development of green and efficient deuteration methods is great significance for various fields such as organic synthesis, analytical chemistry, medicinal chemistry. Herein, we have developed a dehalogenative strategy using piezoelectric materials catalysts in solid‐phase system under ball‐milling conditions. This non‐spontaneous reaction induced by mechanical force. D 2 O can serve both deuterium source an electron donor the transformation, eliminating need additional stoichiometric exogenous reductants. A series (hetero)aryl iodides be transformed into deuterated products with high incorporation. method not only effectively overcomes existing synthetic challenges but also used labelling drug molecules derivatives. Bioactivity experiments molecule suggest that D‐ipriflavone enhances inhibitory effects on osteoclast differentiation BMDMs vitro .

Language: Английский

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions DOI Creative Commons
Federico Cuccu, Lidia De Luca, Francesco Delogu

et al.

ChemSusChem, Journal Year: 2022, Volume and Issue: 15(17)

Published: July 21, 2022

Mechanochemical transformations have made chemists enter unknown territories, forcing a different chemistry perspective. While questioning or revisiting familiar concepts belonging to solution chemistry, mechanochemistry has broken new ground, especially in the panorama of organic synthesis. Not only does it foster "thinking outside box", but also opened reaction paths, allowing overcome weaknesses traditional exactly where use well-established solution-based methodologies rules out progress. In this Review, reader is introduced an intriguing research subject not yet fully explored and waiting for improved understanding. Indeed, study mainly focused on that, although impossible solution, become possible under mechanochemical processing conditions, simultaneously entailing innovation expanding chemical space.

Language: Английский

Citations

185

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 International Edition, Journal Year: 2023, Volume and Issue: 62(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

Citations

27

Advancements and opportunities in piezo-(photo)catalytic synthesis of value-added chemicals DOI Creative Commons
Weiliang Qi, Yaping Fu,

Enbo Liu

et al.

EES Catalysis, Journal Year: 2024, Volume and Issue: 2(4), P. 884 - 910

Published: Jan. 1, 2024

Achieving value-added transformation of chemicals through green catalytic technology can simultaneously meet the market and environmental protection. This article reviews recent advances in synthesizing using piezo-(photo)catalytic technologies.

Language: Английский

Citations

11

Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst DOI

Ruiling Qu,

Shan Wan, Xuemei Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(28)

Published: April 30, 2024

Abstract The development of green and efficient deuteration methods is great significance for various fields such as organic synthesis, analytical chemistry, medicinal chemistry. Herein, we have developed a dehalogenative strategy using piezoelectric materials catalysts in solid‐phase system under ball‐milling conditions. This non‐spontaneous reaction induced by mechanical force. D 2 O can serve both deuterium source an electron donor the transformation, eliminating need additional stoichiometric exogenous reductants. A series (hetero)aryl iodides be transformed into deuterated products with high incorporation. method not only effectively overcomes existing synthetic challenges but also used labelling drug molecules derivatives. Bioactivity experiments molecule suggest that D‐ipriflavone enhances inhibitory effects on osteoclast differentiation BMDMs vitro .

Language: Английский

Citations

9

Piezoelectrically Mediated Reactions: From Catalytic Reactions to Organic Transformations DOI

Ziye Ren,

Yuhao Peng,

Hanliang He

et al.

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 41(1), P. 111 - 128

Published: Sept. 13, 2022

Comprehensive Summary Recently, piezocatalysis has attracted considerable attention as a new type of renewable mechanical energy conversion technology, which relies on the strain induced polarization piezoelectric material. This technology been extensively applied in applications water splitting, remediation, gas purification and tumor therapy. Despite rapid development piezocatalysis, utilization materials for synthetic purpose is still under exploration. Piezoelectric means to promote organic reactions expand scope piezoelectrically mediated show successes both polymer synthesis. Herein, we provide comprehensive review recent progress reactions, catalytic mechanisms last few years. The limitations future directions this area are also discussed. We believe will insights into underlying mechanism electron transfer process guide design chemistry.

Language: Английский

Citations

34

Mechanochemically Induced Cross Dehydrogenative Coupling Reactions under Ball Milling DOI
Ilya N. Egorov, Anindita Mukherjee, Sougata Santra

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(15), P. 2462 - 2478

Published: June 16, 2022

Abstract Cross dehydrogenative coupling (CDC) reactions have become a convenient synthetic strategy for the synthesis of various (het)aromatic scaffolds. In recent times ball milling has emerged as powerful tool to perform in greener way. The current review highlights applications cross under towards useful molecules more efficient and manner. magnified image

Language: Английский

Citations

31

Highlighting the Rich Chemistry of the Allenone Moiety DOI Creative Commons
José M. Alonso, Pedro Almendros

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1332 - 1384

Published: March 14, 2023

Abstract Conjugated and non‐conjugated allenones appear as recurring motifs in organic synthesis, natural products mechanistic investigations showing unique properties applications. The ability of to build cycles has provided a direct access strained systems, medium‐sized rings, arenes, heterocycles complex polycycles. In addition, have served models catalysis. critic compilation herein presented will provide an exhaustive overview the synthetic possibilities may offer, which certainly inspire our community their search more efficient methodologies, preparation biological pharmaceutical targets, improve knowledge theoretical chemistry. Great part this review discuss aspects, catalysis innovation insights chemical transformations implying allenone motif. many examples on total synthesis pharmacologically active compounds be described. We hope that attractive chemistry, catalysis, medicinal chemistry communities. magnified image

Language: Английский

Citations

17

Electro-mechanochemical approach towards the chloro sulfoximidations of allenes under solvent-free conditions in a ball mill DOI
Mostafa M. Amer, Renè Hommelsheim, Christian Schumacher

et al.

Faraday Discussions, Journal Year: 2022, Volume and Issue: 241, P. 79 - 90

Published: June 10, 2022

An electro-mechanochemical protocol for the synthesis of vinylic sulfoximines has been developed. Utilising mechanochemically strained BaTiO3 nanoparticles, catalytic active system is generated in situ by reduction copper(II) chloride. Various combinations electron-donating and -withdrawing groups are tolerated, approach leads to products with difunctionalised double bonds good excellent yields. Attempts add a sulfoximidoyl chloride an alkyne proved difficult. Additions sulfonyl iodide allenes alkynes proceeded smoothly presence silica gel without need activation piezoelectric material.

Language: Английский

Citations

23

Organic Reactions Enabled by Mechanical Force‐Induced Single Electron Transfer DOI
Ruoxuan Liu,

Xiaochun He,

Tianfen Liu

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(47)

Published: June 18, 2024

Mechanochemical reactions, achieved through milling, grinding, or other mechanical actions, have emerged as a solvent-free alternative to traditional solution-based chemistry. Mechanochemistry not only provides the opportunity eliminate bulk solvent use, reducing waste generation, but also unveils new reaction strategy which enables realization of reactions previously inaccessible in solution. While majority organic facilitated by force traditionally follow two-electron transfer pathways similar their counterparts, field mechanochemically induced single-electron (SET) has witnessed rapid development. This review outlines examples mechanochemical SET process, focusing on reagents that initiate SET, thereby positioning mechanochemistry burgeoning within realm

Language: Английский

Citations

6

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

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(49)

Published: Aug. 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.

Language: Английский

Citations

5