Highly Efficient and Recyclable Porous Organic Polymer Supported Iridium Catalysts for Dehydrogenation and Borrowing Hydrogen Reactions in Water

ChemCatChem, Год журнала: 2021, Номер 13(22), С. 4751 - 4758

Опубликована: Сен. 2, 2021

Abstract Benzothiazole‐doped porous organic polymers ( POP‐MBTS ) were synthesized from a copolymerization reaction of 2‐(6‐(4‐vinylphenyl)pyridin‐2‐yl)benzo[ d ]thiazole with divinylbenzene. The corresponding POP‐MBTS‐Ir was obtained and fully characterized using SEM, TEM, EDS, TGA, XPS, N 2 sorption isotherms, which disclosed that this catalyst has high surface area, hierarchical porosity, thermodynamic stability. Importantly, revealed catalytic activity for ten different kinds borrowing hydrogen dehydrogenation reactions in water good recovery performance. Furthermore, mechanistic investigations conducted the synthesis triazine derivatives.

Язык: Английский

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Nickel‐Catalyzed Selective Synthesis of α‐Alkylated Ketones via Dehydrogenative Cross‐Coupling of Primary and Secondary Alcohols

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 364(1), С. 47 - 52

Опубликована: Окт. 11, 2021

Abstract Herein, we describe an isolable, air‐stable, homogeneous, nickel catalyst that performs dehydrogenative cross‐coupling reaction between secondary and primary alcohols to result α‐alkylated ketone products selectively. The sequence of steps involve in this one‐pot is dehydrogenation both alcohols, condensation the aldehyde, hydrogenation situ‐generated α,β‐unsaturated ketone. Preliminary mechanistic investigation hints a radical mechanism following borrowing hydrogen reaction. magnified image

Язык: Английский

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Progressive study on ruthenium catalysis for de(hydrogenative) alkylation and alkenylation using alcohols as a sustainable source

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(41), С. 7998 - 8030

Опубликована: Янв. 1, 2022

This review focuses on the Ru-catalyzed de(hydrogenative) formation of C–C and CC bonds. The comparative reactivity different Ru-complexes to gain selectivity in product is presented, together with brief mechanistic insights.

Язык: Английский

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Recent advances in C/N-alkylation with alcohols through hydride transfer strategies

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(39), С. 7713 - 7745

Опубликована: Янв. 1, 2022

Recent advances in C/N alkylation using alcohols as alkylating reagents via hydrogen-shuttle methodologies: Borrowing Hydrogen, Acceptorless Dehydrogenative Coupling, and Base-mediated Hydride Transfer.

Язык: Английский

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Direct couplings of secondary alcohols with primary alkenyl alcohols to α-alkylated ketones via a tandem transfer hydrogenation/hydrogen autotransfer process catalyzed by a metal-ligand bifunctional iridium catalyst

Journal of Catalysis, Год журнала: 2022, Номер 413, С. 365 - 373

Опубликована: Июнь 25, 2022

Язык: Английский

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NNN Pincer-Manganese-Catalyzed Guerbet-Type β-Alkylation of Alcohols under Microwave Irradiation

Organometallics, Год журнала: 2023, Номер 42(14), С. 1818 - 1831

Опубликована: Июнь 24, 2023

A series of manganese carbonyl complexes based on bis(imino)pyridine ligands the type R2NNN (R = Cy, iPr, Ph, p-FC6H4) were synthesized. While complex appears to be an NN bidentate-Mn(I) triscarbonyl species in solid state, solution, there is a gradual loss carbon monoxide leading first NNN pincer-Mn(I) biscarbonyl complex, which finally disproportionates pincer-Mn(II) dibromide and pincer-Mn(0) complex. Evidence for this transformation has been obtained from single-crystal X-ray diffraction, IR, EPR, HRMS analysis. The apparently faster with cyclohexyl-substituted than others. considered (0.05 mol %) utilized catalyzing β-alkylation secondary alcohols at 140 °C air under conventional heating (12 h), as well microwave (2 h) presence 2.5 % NaOtBu. Among complexes, catalyst (p-FC6H4NNN)Mn(CO)2Br was found highly efficient. heating, maximum 92% (1840 TON 153 TOs/h) β-alkylated product obtained; provided 85% yield (1700 850 just 2 h. catalytic system successfully implemented alkylate several other alcohols, (35 examples). analyses indicate intermediates cycle both pincer-Mn(II)/Mn(0) couple. Deuterium labeling studies point involvement C–H bond activation rate-determining step (RDS) kinetic isotope effect (KIE) 9.0.

Язык: Английский

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Hydrogenation and Cross-Coupling Reactions Catalyzed by Mn, Fe, and Co Aromatic Pincer Complexes

Organometallics, Год журнала: 2023, Номер 42(18), С. 2426 - 2446

Опубликована: Сен. 8, 2023

Currently, the development of environmentally benign and effective catalytic reactions for organic synthesis based on low-cost abundant metals is one central research goals in modern chemistry. This review covers advancements homogeneously catalyzed using pincer complexes manganese, iron, cobalt featuring aryl pyridine backbones. Specifically, C–C coupling hydrogenation alkenes, alkynes, aldehydes, ketones, esters, nitriles, CO2, carbamates, ureas, cyclic imides azo compounds are described, including their scope mechanistic insights. Overall, this emphasizes that combination inexpensive readily available metals, such as Mn, Fe, Co, with ligands capable ligand–metal cooperation may lead to creation innovative, versatile, catalysts, some which can even exceed activity state-of-the-art noble-metal systems green chemistry processes.

Язык: Английский

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Highly Efficient Base Catalyzed N‐alkylation of Amines with Alcohols and β‐Alkylation of Secondary Alcohols with Primary Alcohols

ChemCatChem, Год журнала: 2023, Номер 15(20)

Опубликована: Авг. 8, 2023

Abstract Borrowing hydrogen (BH) reactions are very useful for the sustainable synthesis of C−C and C−N bonds. They generally operate with transition metal‐based catalysts along stoichiometric/catalytic amounts added base. Here we report that two catalytic transformations, carried out BH methodology, i. e. N ‐alkylation amines alcohols β‐alkylation secondary primary alcohols, can be performed effectively just base under air without using any catalyst. The mechanism is proposed to based on oxidation alcohol aldehyde followed by condensation an unsaturated intermediate which undergoes transfer hydrogenation product.

Язык: Английский

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Designing Cobalt(II) Complex for Chemoselective Synthesis of 2‐Aryl‐3‐Formyl Indoles from Amino Alcohols and Alcohols^†

Chemistry - A European Journal, Год журнала: 2024, Номер 30(47)

Опубликована: Июнь 20, 2024

An air-stable, inexpensive, and isolable cobalt(II) complex (C1) of N-((1-methyl-1H-imidazol-2-yl)methyl)-2-(phenylselanyl)ethan amine (L1) was synthesized characterized. The used to catalyze a one-pot cascade reaction between 2-(2-aminophenyl)ethanols benzyl alcohol derivatives. Interestingly, 2-aryl-3-formylindole derivatives were formed instead N-alkylated or C-3 alkylated indoles. A broad substrate scope can be activated using this protocol with only 5.0 mol % catalyst loading achieve up 87 yield mechanistic studies suggested that the proceeds through tandem imine formation followed by cyclization.

Язык: Английский

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Manganese(I)-NNSe Pincer Complex Mediated Dehydrogenative Cyclization to Synthesize 2-Aryl-2,3-dihydroquinolin-4(1H)-ones

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 28, 2025

A catalytic one-pot cascade dehydrogenative cyclization of 1-(2-aminophenyl)ethanone using primary alcohols is presented. The reaction catalyzed by an earth-abundant manganese pincer complex NNSe ligand, without any solvent, additives, base, or hydrogen acceptor, liberating dihydrogen and water as the only byproducts. Compared to earlier reported four-step coupling protocol, a single step required synthesize 2-aryl-2,3-dihydroquinolin-4(1H)-ones.

Язык: Английский

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