A Phosphine-Free Air-Stable Mn(II)-Catalyst for Sustainable Synthesis of Quinazolin-4(3H)-ones, Quinolines, and Quinoxalines in Water DOI
Sucheta Mondal, Subhajit Chakraborty,

Subhankar Khanra

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5250 - 5265

Опубликована: Март 30, 2024

The synthesis, characterization, and catalytic application of a new phosphine-free, well-defined, water-soluble, air-stable Mn(II)-catalyst [Mn(L)(H2O)2Cl](Cl) ([1]Cl) featuring 1,10-phenanthroline based tridentate pincer ligand, 2-(1H-pyrazol-1-yl)-1,10-phenanthroline (L), in dehydrogenative functionalization alcohols to various N-heterocycles such as quinazolin-4(3H)-ones, quinolines, quinoxalines are reported here. A wide array multisubstituted quinazolin-4(3H)-ones were prepared water under air following two pathways via the coupling with 2-aminobenzamides 2-aminobenzonitriles, respectively. 2-Aminobenzyl alcohol ketones bearing active methylene group used partners for synthesizing quinoline derivatives, quinoxaline derivatives by vicinal diols 1,2-diamines. In all cases, reaction proceeded smoothly using our [1]Cl air, affording desired satisfactory yields starting from cheap readily accessible precursors. Gram-scale synthesis compounds indicates industrial relevance synthetic strategy. Control experiments performed understand unveil plausible mechanism.

Язык: Английский

Homogeneous manganese-catalyzed hydrogenation and dehydrogenation reactions DOI Creative Commons
Yujie Wang, Mingyang Wang, Yibiao Li

и другие.

Chem, Год журнала: 2020, Номер 7(5), С. 1180 - 1223

Опубликована: Дек. 9, 2020

Язык: Английский

Процитировано

220

Manganese-catalyzed hydrogenation, dehydrogenation, and hydroelementation reactions DOI
Kuhali Das, Satyadeep Waiba, Akash Jana

и другие.

Chemical Society Reviews, Год журнала: 2022, Номер 51(11), С. 4386 - 4464

Опубликована: Янв. 1, 2022

The emerging field of organometallic catalysis has shifted towards research on Earth-abundant transition metals due to their ready availability, economic advantage, and novel properties. In this case, manganese, the third most abundant transition-metal in Earth's crust, emerged as one leading competitors. Accordingly, a large number molecularly-defined Mn-complexes been synthesized employed for hydrogenation, dehydrogenation, hydroelementation reactions. regard, catalyst design is based three pillars, namely, metal-ligand bifunctionality, ligand hemilability, redox activity. Indeed, developed catalysts not only differ chelating atoms they possess but also working principles, thereby different turnover numbers product molecules. Hence, critical assessment molecularly defined manganese terms atoms, reaction conditions, mechanistic pathway, significant. Herein, we analyze complexes catalytic activity, versatility allow multiple transformations routes convert substrates target This article will be helpful get significant insight into design, aiding design.

Язык: Английский

Процитировано

163

Homogeneously catalyzed acceptorless dehydrogenation of alcohols: A progress report DOI Creative Commons
Mónica Trincado,

Jonas Bösken,

Hansjörg Grützmacher

и другие.

Coordination Chemistry Reviews, Год журнала: 2021, Номер 443, С. 213967 - 213967

Опубликована: Май 24, 2021

Catalytic dehydrogenation of alcohols represents an attractive approach for future applications as hydrogen storage systems and clean synthesis fine chemicals. Herein, overview recent progress in homogeneously catalyzed acceptorless alcohol is presented. In Nature, efficiently by multiple metalloenzymes where a non-noble metal–ligand interplay key to activate transform substrate. We highlight the introduction multifunctional cooperative ligands coordination sphere metal center order improve catalytic activity under photochemical, electrochemical or thermal conditions. Moreover, cooperativity crucial easy transition first row based catalysis, we have seen years.

Язык: Английский

Процитировано

115

Ketones as strategic building blocks for the synthesis of natural product-inspired compounds DOI
Daniel J. Foley, Herbert Waldmann

Chemical Society Reviews, Год журнала: 2022, Номер 51(10), С. 4094 - 4120

Опубликована: Янв. 1, 2022

This review explores and summarises synthetic methods that may be used to prepare heterocyclic ring systems from non-activated ketones, considers their potential value towards the synthesis of natural product-inspired compound collections.

Язык: Английский

Процитировано

83

Transition metals-catalyzed amination of biomass feedstocks for sustainable construction of N-heterocycles DOI
Qiong Yan, Xu Wu, Hao Jiang

и другие.

Coordination Chemistry Reviews, Год журнала: 2023, Номер 502, С. 215622 - 215622

Опубликована: Дек. 26, 2023

Язык: Английский

Процитировано

81

Recent Progress with Pincer Transition Metal Catalysts for Sustainability DOI Open Access
Luca Piccirilli, Danielle L. J. Pinheiro, Martin Nielsen

и другие.

Catalysts, Год журнала: 2020, Номер 10(7), С. 773 - 773

Опубликована: Июль 11, 2020

Our planet urgently needs sustainable solutions to alleviate the anthropogenic global warming and climate change. Homogeneous catalysis has potential play a fundamental role in this process, providing novel, efficient, at same time eco-friendly routes for both chemicals energy production. In particular, pincer-type ligation shows promising properties terms of long-term stability selectivity, as well allowing mild reaction conditions low catalyst loading. Indeed, pincer complexes have been applied plethora chemical processes, such hydrogen release, CO2 capture conversion, N2 fixation, biomass valorization synthesis high-value fuels. work, we show main advances last five years use transition metal key catalytic processes aiming more

Язык: Английский

Процитировано

97

Manganese Catalyzed Acceptorless Dehydrogenative Coupling Reactions DOI
Satyadeep Waiba, Biplab Maji

ChemCatChem, Год журнала: 2019, Номер 12(7), С. 1891 - 1902

Опубликована: Дек. 21, 2019

Abstract Acceptorless dehydrogenative coupling (ADC) has emerged as a powerful tool in the chemists’ arsenal for construction of various carbon‐carbon and carbon‐heteroatom bonds. These protocols are highly atom economical environmentally benign they do not require pre‐functionalized starting material produce only dihydrogen (and water) by‐product. This technique, coupled with Earths’ abundant less toxic manganese catalysis, can prove to be vital strategy generation molecular complexity from simple materials. Manganese catalyzed DHC been growing interest, low‐ high‐valent catalysts have developed. were demonstrated show excellent catalytic activity formation carbon‐carbon, bonds, cascade reactions. In this mini‐review, we would like highlight recent progress that made ADC

Язык: Английский

Процитировано

95

Recent advancement in oxidation or acceptorless dehydrogenation of alcohols to valorised products using manganese based catalysts DOI
Prakash Chandra,

Topi Ghosh,

Neha Choudhary

и другие.

Coordination Chemistry Reviews, Год журнала: 2020, Номер 411, С. 213241 - 213241

Опубликована: Март 4, 2020

Язык: Английский

Процитировано

82

Mechanism of the Manganese-Pincer-Catalyzed Acceptorless Dehydrogenative Coupling of Nitriles and Alcohols DOI
Jesús Antonio Luque‐Urrutia, Miquel Solà, David Milstein

и другие.

Journal of the American Chemical Society, Год журнала: 2019, Номер 141(6), С. 2398 - 2403

Опубликована: Янв. 11, 2019

A recent study showed that a Mn-pincer could catalyze the acceptorless dehydrogenative coupling of nitriles and alcohols to yield acrylonitriles. The reaction mechanism proposed in work contained some intermediates that, most cases, were not characterized. Moreover, one involved charged separation, which is unlikely apolar solvents. To clarify this critical reaction, we decided perform DFT study. Our results prove existence cooperative effect metal ligand several steps catalytic cycle. We also find presence equilibria between isomeric where water, or same alcohol reagent, takes part assisting proton transfer. Furthermore, have analyzed charge-separated structure experimentally found nearly pure covalent bond two expected moieties. Finally, Knoevenagel condensation step generates acrylonitrile be rate-determining step.

Язык: Английский

Процитировано

81

Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis DOI

Jannik C. Borghs,

Mai Anh Tran,

Jan Sklyaruk

и другие.

The Journal of Organic Chemistry, Год журнала: 2019, Номер 84(12), С. 7927 - 7935

Опубликована: Май 22, 2019

A general and chemoselective catalytic alkylation of nitriles using a homogeneous nonprecious manganese catalyst is presented. This reaction uses naturally abundant alcohols readily available as coupling partners. The tolerates wide range functional groups heterocyclic moieties, efficiently providing useful cyanoalkylated products with water the only side product. Importantly, methanol can be used C1 source C-methylation achieved. mechanistic investigations support multiple role metal-ligand catalyst, dehydrogenative activation alcohol, α-C-H nitrile, hydrogenation in-situ-formed unsaturated intermediate.

Язык: Английский

Процитировано

81