Journal of Inclusion Phenomena and Macrocyclic Chemistry, Journal Year: 2023, Volume and Issue: unknown
Published: Dec. 25, 2023
Language: Английский
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(28), P. 5671 - 5690
Published: Jan. 1, 2023
This review discusses known approaches for selective pyridine C–H editing, focusing on recent discoveries uniquely suited to pyridines.
Language: Английский
Citations
31
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
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: March 3, 2025
We report the photocatalyzed three-component alkene 1,2-alkylpyridylation reaction between alkylboronic acids, 4-cyanopyridine, and an olefin to achieve pyridination alkylation of synthesis structurally diversified 4-alkylpyridines. The readily available easily manipulated acids were used as alkyl radical precursors. reactions take place under mild conditions with a broad substrate scope are easy scale up gram level, they therefore potential practical value for structural modification biologically active alkylpyridine derivatives.
Language: Английский
Citations
0
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(39)
Published: June 30, 2023
Organomagnesium halides (Grignard reagents) are essential carbanionic building blocks widely used in carbon-carbon and carbon-heteroatom bond-forming reactions with various electrophiles. In the Barbier variant of Grignard synthesis, generation air- moisture-sensitive reagents occurs concurrently their reaction an electrophile. Although operationally simpler, classic approach suffers from low yields due to multiple side reactions, thereby limiting scope its application. Here, we report a mechanochemical adaptation Mg-mediated reaction, which overcomes these limitations facilitates coupling versatile organic (e.g., allylic, vinylic, aromatic, aliphatic) diverse range electrophilic substrates aromatic aldehydes, ketones, esters, amides, O-benzoyl hydroxylamine, chlorosilane, borate ester) assemble C-C, C-N, C-Si, C-B bonds. The has advantage being essentially solvent-free, simple, immune air, surprisingly tolerant water some weak Brønsted acids. Notably, solid ammonium chloride was found improve ketones. Mechanistic studies have clarified role mechanochemistry process, indicating transient organometallics facilitated by improved mass transfer activation surface magnesium metal.
Language: Английский
Citations
8
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(7), P. 1509 - 1516
Published: Feb. 19, 2024
Abstract The reaction of chlorosilanes with organometallic reagents is an old and well‐developed approach to organosilicon compounds, however, its application was limited due the sensitivity air, water. Here we display a mechanochemical access arylsilanes via Barbier‐type aryl halide magnesium. By treatment two halides Mg powder under electromagnetic milling, series are obtained within 15 minutes. Taking advantages this protocol features transition‐metal free, good functional group tolerance, air stable mild conditions.
Language: Английский
Citations
2
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(26)
Published: Jan. 31, 2024
Although the 3 d transition-metal catalyzed C-H functionalization have been extensively employed to promote formation of valuable carbon-carbon bonds, persistent problems, including use sensitive Grignard reagents and rigorous operations (solvent-drying, inert gas protection, metal pre-activation RMgX addition rate control), still leave great room for further development sustainable methodologies. Herein, we report a mechanochemical technology toward in-situ preparation highly organomagnesium reagents, thus building two general catalytic platforms that enables regioselective arylation alkylation indoles with wide variety halides (including those containing post transformable functionalities heteroaromatic rings). This strategy also brings unique reactivity high step-economy in producing functionalized N-free indole products.
Language: Английский
Citations
2
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7148 - 7155
Published: May 8, 2024
Alkyl- and arylpyridines 2,2′-bipyridines are conventionally prepared by Minisci reactions of pyridines transition metal-catalyzed coupling halopyridines. Herein, purple light-promoted radical 2- or 4-bromopyridines with Grignard reagents in Et2O a mixture tetrahydrofuran regular glassware without the need for metal catalyst were disclosed first time. Methyl, primary secondary alkyl, cycloalkyl, aryl, heteroaryl, pyridyl, alkynyl compatible protocol. As result, alkyl- easily prepared. Single electron transfer from reagent to bromopyridine was stimulated light. An extruded dimerization worked as catalyst. Light on/off experiments indicated that constant irradiation required product formation. Studies clock substrates verified involvement pyridyl noninvolvement an alkyl aryl reagent. The available proof supports photoinduced SRN mechanism new reactions.
Language: Английский
Citations
2
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3849 - 3854
Published: Jan. 1, 2024
A regioselective para -alkylation of pyridines using alkyl carboxylic acid-derived diacyl peroxides or peresters is reported. This reaction proceeds under mild conditions, and late-stage functionalization complex can be realized.
Language: Английский
Citations
2
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(44)
Published: July 30, 2024
Abstract Excited states of radical anions derived from the photoreduction stable organic molecules are suggested to serve as potent reductants. However, excited these species too short‐lived allow bimolecular quenching processes. Recently, singlet state Meisenheimer complexes, which possess a long‐lived state, was identified competent for reduction challenging substrates (−2.63 V vs. SCE, saturated calomel electrode). To produce reasonably and simply accessible different addition n BuLi readily available aromatic heterocycles investigated, photoreactivity generated studied. In this paper, we present straightforward preparation family powerful photoreductants (*E ox < −3 SCE in their states, determined by DFT time‐dependent TD‐DFT calculations; DFT, density functional theory) that can induce dehalogenation electron‐rich aryl chlorides form C−C bond through cyclization. Photophysical analyses computational studies combination with experimental mechanistic investigations demonstrate ability adduct act strong electron donor under visible light irradiation.
Language: Английский
Citations
2
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 127 - 134
Published: Nov. 10, 2023
A mechanochemical iron-catalyzed asymmetric oxidative coupling between glycines and β-ketoesters has been disclosed, utilizing t -BuOH to improve the enantioselectivity stabilize iminium intermediate via intensified hydrogen bond interactions.
Language: Английский
Citations
4