Ball-milling-enabled nickel-catalyzed radical relayed reductive cross-coupling DOI Creative Commons
Chunying Fan, Bobo Wang, Tianle Wu

et al.

Cell Reports Physical Science, Journal Year: 2024, Volume and Issue: 5(2), P. 101831 - 101831

Published: Feb. 1, 2024

Nickel-catalyzed radical relayed dicarbofunctionalizations of olefins, utilizing carbon electrophiles as coupling partners, present a powerful strategy for the streamlined construction aliphatic structures. However, traditional solution-phase methods encounter challenges such need bulk solvents, limited long reaction times, and air-/moisture-sensitive reagents. As an alternative strategy, ball-mill-enabled metal-catalyzed cross-coupling reactions have gained attention due to their high reactivity atomic efficiency. While many are single- two-component methodologies, three-component solid-state remain relatively scarce. In this work, we report first, our knowledge, ball-milling-enabled Ni-catalyzed reductive dicarbofunctionalization alkenes. Two distinct readily available electrophiles, Csp2 Csp3 halides, simultaneously installed across variety olefins at room temperature in highly regioselective manner withing 1.5 h. By harnessing benefits ball milling reactions, anticipate further advancements sustainable efficient synthetic methodologies.

Language: Английский

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
Mechanochemistry enabling highly efficient Birch reduction using sodium lumps and d-(+)-glucose DOI Creative Commons

Keisuke Kondo,

Koji Kubota, Hajime Ito

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(12), P. 4452 - 4457

Published: Jan. 1, 2024

In this study, a mechanochemical protocol for highly efficient and ammonia-free sodium-based Birch reduction was developed, leveraging the use of cheap easy-to-handle sodium lumps d -(+)-glucose as proton source.

Language: Английский

Citations

14
Mechanophotocatalysis: A Generalizable Approach to Solvent‐minimized Photocatalytic Reactions for Organic Synthesis DOI Creative Commons
Francis Millward, Eli Zysman‐Colman

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(13)

Published: Jan. 24, 2024

This proof-of-concept study cements the viability and generality of mechanophotocatalysis, merging mechanochemistry photocatalysis to enable solvent-minimized photocatalytic reactions. We demonstrate transmutation four archetypal solution-state reactions a environment driven by combined actions milling, light, photocatalysts. The chlorosulfonylation alkenes pinacol coupling aldehydes ketones were conducted under solvent-free conditions with competitive or superior efficiencies their analogues. Furthermore, decarboxylative alkylations are shown function efficiently conditions, while photoinduced energy transfer promoted [2+2] cycloaddition chalcone experiences significant initial rate enhancement over its variant. work serves as platform for future discoveries in an underexplored field: validating that is not only generalizable photocatalysis, but can also offer valuable advantages.

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
Mechanosynthesis of Pyrrole-2-carboxylic Acids via Copper-Catalyzed Spiroannulation/Ring-Opening Aromatization of 4-Arylidene Isoxazol-5-ones with Enamino Esters DOI
Mingjun Li,

Hui-Juan Xiao,

Peng Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4189 - 4193

Published: May 14, 2024

An efficient and practical tandem reaction of 4-arylidene isoxazol-5-ones with enamino esters catalyzed by an inexpensive copper salt has been established in a ball mill. This innovative approach yields diverse array structurally novel pyrrole-2-carboxylic acids, showing excellent tolerance toward different functional groups. By integrating spiroannulation ring-opening aromatization processes, this protocol introduces facile cost-effective strategy for synthesizing highly functionalized pyrrole derivatives.

Language: Английский

Citations

9
Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials DOI
Yumei Wang,

Ziwu Zhang,

Lichan Deng

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(18), P. 7171 - 7176

Published: Aug. 30, 2021

A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as piezoelectric material in this transformation. This method features no usage solvent, experimental operation, scalable potential, high conversion efficiency, which make it attractive practical.

Language: Английский

Citations

55
Mechanochemical Solvent‐Free Suzuki–Miyaura Cross‐Coupling of Amides via Highly Chemoselective N−C Cleavage DOI
Jin Zhang, Pei Zhang, Lei Shao

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(7)

Published: Dec. 8, 2021

Although cross-coupling reactions of amides by selective N-C cleavage are one the most powerful and burgeoning areas in organic synthesis due to ubiquity amide bonds, development mechanochemical, solid-state methods remains a major challenge. Herein, we report first mechanochemical strategy for highly chemoselective, solvent-free palladium-catalyzed bond activation. The method is conducted absence external heating, short reaction time shows excellent chemoselectivity σ functional group tolerance can be applied late-stage functionalization complex APIs sequential orthogonal cross-couplings exploiting double solventless methods. results extend environments advance chemical repertoire interconversions environmentally friendly

Language: Английский

Citations

42
Diaryliodonium salts facilitate metal-free mechanoredox free radical polymerizations DOI Creative Commons
Sarah M. Zeitler, Progyateg Chakma, Matthew R. Golder

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(14), P. 4131 - 4138

Published: Jan. 1, 2022

Mechanically-induced redox processes offer a promising alternative to more conventional thermal and photochemical synthetic methods.

Language: Английский

Citations

37
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
Mechanochemical protocol facilitates the generation of arylmanganese nucleophiles from unactivated manganese metal DOI Creative Commons
Rina Takahashi, Pan Gao, Koji Kubota

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 14(3), P. 499 - 505

Published: Nov. 28, 2022

The direct synthesis of organomanganese reagents from organic halides and manganese metal remains a challenge. Current solution-based approaches require the preparation activated (Rieke manganese) or use multiple additives to promote insertion into carbon-halogen bond. Here, we show that mechanochemical ball-milling protocol facilitates generation various arylmanganese nucleophiles aryl commercially available, unactivated without need for complicated pre-activation processes additives. These manganese-based carbon can be used directly one-pot addition reactions with electrophiles palladium-catalyzed cross-coupling under bulk-solvent-free conditions. Importantly, all experimental operations conducted atmospheric

Language: Английский

Citations

30