Mechanochemical Cascade Cyclization of Cyclopropyl Ketones with 1,2-Diamino Arenes for the Direct Synthesis of 1,2-Disubstituted Benzimidazoles DOI
Srinivasarao Yaragorla,

Divyanshu Tiwari,

Mehak Saba Lone

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(13), С. 9427 - 9439

Опубликована: Июнь 21, 2024

A mechanochemical synthesis of 1,2-disubstituted benzimidazoles from donor-acceptor cyclopropyl ketones and 1,2-diaminoarenes under metal-free solventless conditions is reported. The reaction does not require inert promoted by a stoichiometric amount 1,1,1,3,3,3-hexafluoroisopropanol. This cascade involves ring-opening, cyclization, retro-Mannich with aryl 1,2-diamines. Compared to its solution-phase counterpart, this approach shows fast reactivity (24 vs 1.5 h). Mechanistic investigations electrospray ionization mass spectrometry helped us propose the mechanism.

Язык: Английский

Boosting tribo-catalytic conversion of H 2O and CO 2 by Co 3O 4 nanoparticles through metallic coatings in reactors DOI Creative Commons

Xuchao Jia,

Hongbo Wang, Lei Hua

и другие.

Journal of Advanced Ceramics, Год журнала: 2023, Номер 12(10), С. 1833 - 1843

Опубликована: Июль 26, 2023

In recent years, more and metal oxides have been finding critical tribo-catalytic applications. Presently, we explored the conversion of H2O CO2 using Co3O4 nanoparticles obtained some surprising results. an as-received 150 mL glass reactor enclosed with 10 H2O, 0.10 g nanoparticles, 1 atm CO2, a Teflon magnetic rotary disk, observed production as much 57.41 µmol/L H2, 0.15 CH4, 0.21 CO after 5 h stirring. Metallic coatings Cu, Ni, SUS316, Ti, Nb, Mo, W were further introduced on bottoms separately. For those reduction was dramatically enhanced C2+ products C2H6 C2H4 observed. Especially for Ti coating, amounts H2 CH4 increased by 2 26 times from bottom, respectively, very impressive. proven chemically stable under stirring in water, hydroxyl radicals superoxide detected through fluorescence spectroscopy electron paramagnetic resonance analyses. These findings not only reveal outstanding capability to generate multicarbon tribo-catalysis but also highlight promising potential whole harness mechanical energy addressing shortages environmental pollution.

Язык: Английский

Процитировано

19

Opportunities and Challenges in Applying Solid‐State NMR Spectroscopy in Organic Mechanochemistry DOI Creative Commons
Igor d’Anciães Almeida Silva, Ettore Bartalucci, Carsten Bolm

и другие.

Advanced Materials, Год журнала: 2023, Номер 35(52)

Опубликована: Июль 5, 2023

In recent years it is shown that mechanochemical strategies can be beneficial in directed conversions of organic compounds. Finding new reactions proved difficult, and due to the lack mechanistic understanding reaction events, respective efforts have mostly remained empirical. Spectroscopic techniques are crucial shedding light on these questions. this overview, opportunities challenges solid-state nuclear magnetic resonance (NMR) spectroscopy field mechanochemistry discussed. After a brief discussion basics high-resolution NMR under magic-angle spinning (MAS) conditions, seven for presented, ranging from ex situ approaches structurally elucidated products obtained by milling potential limitations approaches. Particular strengths NMR, instance differentiating polymorphs, NMR-crystallographic structure-determination protocols, or detecting weak noncovalent interactions molecular-recognition events employing proton-detected experiments at fast MAS frequencies,

Язык: Английский

Процитировано

18

Mechanochemical Birch Reduction with Low Reactive Alkaline Earth Metals DOI
Jagadeesh Varma Nallaparaju,

Riin Satsi,

Danylo Merzhyievskyi

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(20)

Опубликована: Март 4, 2024

Abstract Birch reduction and similar dissolved metal‐type transformations hold significant importance in the organic synthesis toolbox. Historically, field has been dominated by alkali metal reductants. In this study, we report that largely neglected, low‐reactive alkaline earth metals can become powerful affordable reductants when used a ball mill under essentially solvent‐free conditions, presence of ethylenediamine THF as liquid additives. Calcium reduce both electron‐deficient electron‐rich arenes, with yields products to those obtained lithium metal. Magnesium reveals enhanced reducing power, enabling benzoic acids while keeping aromatic moieties intact allows for chemoselective transformations. The developed mechanochemical approach uses readily available safer‐to‐handle metals, operates air ambient temperature be gram‐scale preparations. Finally, demonstrate conditions other reductive transformations, including amination, deoxygenation, dehalogenation, alkene alkyne reductions.

Язык: Английский

Процитировано

8

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

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(28)

Опубликована: Апрель 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 .

Язык: Английский

Процитировано

8

Mechanochemical Cascade Cyclization of Cyclopropyl Ketones with 1,2-Diamino Arenes for the Direct Synthesis of 1,2-Disubstituted Benzimidazoles DOI
Srinivasarao Yaragorla,

Divyanshu Tiwari,

Mehak Saba Lone

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(13), С. 9427 - 9439

Опубликована: Июнь 21, 2024

A mechanochemical synthesis of 1,2-disubstituted benzimidazoles from donor-acceptor cyclopropyl ketones and 1,2-diaminoarenes under metal-free solventless conditions is reported. The reaction does not require inert promoted by a stoichiometric amount 1,1,1,3,3,3-hexafluoroisopropanol. This cascade involves ring-opening, cyclization, retro-Mannich with aryl 1,2-diamines. Compared to its solution-phase counterpart, this approach shows fast reactivity (24 vs 1.5 h). Mechanistic investigations electrospray ionization mass spectrometry helped us propose the mechanism.

Язык: Английский

Процитировано

8