Article
Chemistry, Organic
Swadhin Chetia, Samprity Sarmah, Apurba Dutta, Diganta Sarma
Summary: A copper acetate monohydrate catalyzed protocol for the construction of quinazoline derivatives and quinolines analogues via dehydrogenative coupling of 2-aminoaryl methanols and nitriles is developed. The reaction proceeded in toluene at 110 degrees C for 5 h without the requirement of inert condition, external additives, and ligands.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hongling Shui, Yuhong Zhong, Lu Ouyang, Nianhua Luo, Renshi Luo
Summary: An efficient iridium-catalyzed acceptorless dehydrogenative coupling (ADC) reaction has been developed for the preparation of various quinazolines from 2-aminoarylmethanols and amides or nitriles. The method offers high atom economy, mild reaction conditions, simple operation, and is suitable for a variety of substrates.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Physical
Gunasekaran Balamurugan, Rengan Ramesh
Summary: A new nickel complex catalyst is used for the synthesis of (E)-olefins via greener acceptorless dehydrogenative coupling methodology. This simple and efficient protocol is applicable to a wide range of substrates, including drug intermediates.
Article
Chemistry, Organic
Aubin Charvieux, Abdul Aziz Hammoud, Marie-Christine Duclos, Nicolas Duguet, Estelle Metay
Summary: A high atom-economical method for the formation of indoles from anilines and diols was successfully achieved using affordable and easy-to-handle Ni/SiO2-Al2O3. The reaction resulted in excellent yields of 2,3-dimethylindole with good scope and versatility.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Applied
Saranya Sundar, Ramesh Rengan, Anandaraj Pennamuthiriyan, David Semeril
Summary: A facile catalytic one-pot synthesis of N-acylhydrazones has been described using arene ruthenium (II) complexes. The method provides a wide range of N-acylhydrazones in good yields with high selectivity and functional group tolerance, without any alkylated products.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yaoyu Liang, Jie Luo, David Milstein
Summary: In this study, a new reaction of acceptorless dehydrogenative coupling of epoxides and amines to form amides catalyzed by ruthenium pincer complexes is reported. This reaction shows high yield and selectivity, and is significant in various academic and industrial fields.
Article
Chemistry, Organic
Gargi Chakraborty, Rakesh Mondal, Amit Kumar Guin, Nanda D. Paul
Summary: In this study, a nickel-catalyzed sustainable synthesis method was utilized to prepare a variety of five-membered fused nitrogen heterocycles, including benzimidazole, purine, benzothiazole, and benzoxazole. This was achieved through acceptorless dehydrogenative functionalization of alcohols and borrowing hydrogen approach, using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst. Control experiments were conducted to elucidate the reaction mechanism.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Nihal S. Tabasi, Sertac Genc, Derya Gulcemal
Summary: An acceptorless dehydrogenative coupling of primary alcohols to carboxylic acids/carboxylates, esters, and Guerbet alcohols was developed under aerobic conditions using an N-heterocyclic carbene iridium(i) catalyst. The selectivity of the products can be easily adjusted by modifying reaction conditions such as catalyst and base amounts, choice of base, and reaction temperature.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Physical
Shuaicong Huo, Siqi Kong, Guang Zeng, Qi Feng, Zhiqiang Hao, Zhangang Han, Jin Lin, Guo-Liang Lu
Summary: Treatment of N,N,O-tridentate pyrazolyl-pyridinyl-alcohol ligands with RuCl3.xH(2)O in refluxing EtOH afforded Ru(III) complexes, which showed high catalytic performance for dehydrogenative couplings of 2-aminoarylmethanols with ketones and nitriles, providing a sustainable route to access various structurally important quinoline and quinazoline derivatives.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Organic
Nandita Biswas, Dipankar Srimani
Summary: The Ru-catalyzed reaction provides an economical and simple operational strategy for synthesizing biologically active 1,8-dioxodecahydroacridine derivatives with a wide substrate scope and good tolerance toward various functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yik Ki Au, Qiangqiang Ma, Jie Zhang, Zuowei Xie
Summary: An efficient and convenient strategy for Ir-catalyzed selective B(3)-amination of o-carboranes with amines via acceptorless BH/NH dehydrocoupling was developed, resulting in a series of B(3)-aminated-o-carboranes with moderate to high yields and H2 gas as the sole by-product. The oxidant-free system demonstrates sustainability, atom-economy, and environmental friendliness. A reaction mechanism involving an Ir(I)-Ir(III)-Ir(I) catalytic cycle with oxidative addition, dehydrogenation, and reductive elimination was proposed.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Mingshi Pan, Xiabin Wang, Yixin Tong, Xiaodong Qiu, Xiaobao Zeng, Biao Xiong
Summary: A new strategy for the direct synthesis of functionalized pyrroles from beta-amino alcohols and ynones has been demonstrated. This method proceeds in an atom- and step-economic fashion and offers the advantages of broad substrate scope, operational simplicity, and water and hydrogen gas as the sole by-products, providing an alternative and sustainable path to access functionalized pyrroles.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Dipanjan Bhattacharyya, Priyanka Adhikari, Kritartha Deori, Animesh Das
Summary: The synthesis of N-heterocycles is important in pharmaceuticals, materials science, and natural product synthesis. This study presents an efficient method for the synthesis of quinoline and quinazoline derivatives through an alcohol-catalyzed acceptorless dehydrogenative coupling (ADC). The use of a bifunctional ruthenium NNN-pincer complex as the catalyst allows the synthesis of a wide range of substituted quinolines and quinazolines with high yields and selectivity.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Organic
Yanling Zheng, Yang Long, Huihua Gong, Jiaqi Xu, Chunchun Zhang, Haiyan Fu, Xueli Zheng, Hua Chen, Ruixiang Li
Summary: In this study, the divergent transformations of 1,3-diols with arylhydrazines were reported, which selectively synthesized pyrazoles and 2-pyrazolines via acceptorless dehydrogenative coupling reactions using Ru3(CO)12/NHC-phosphinephosphine catalytic systems. The reactions showed low catalyst loading, high selectivity, wide substrate scope, and good yields, with only water and hydrogen gas (H2) as the byproducts.
Review
Chemistry, Organic
Bivas Chandra Roy, Kasturi Ganguli, Sk. Abdus Samim, Sabuj Kundu
Summary: Alcohol has garnered special attention in the past two decades due to its abundance, low cost, and low toxicity, making it a versatile building block for synthesizing value-added products. Metal-ligand cooperation is a powerful tool for utilizing alcohol in the synthesis of complex molecules. This review focuses on stable metal-ligand cooperative 5d, 4d, and 3d metal-based complexes for effective alcohol dehydrogenative coupling reactions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Rakesh Mondal, Amit Kumar Guin, Subhajit Chakraborty, Nanda D. Paul
Summary: Here, we report a metal-ligand cooperative approach for the sustainable synthesis of various aldazines, ketazines, and N-acylhydrazones through the dehydrogenative functionalization of alcohols with hydrazine hydrate using a simple iron catalyst featuring a redox noninnocent tridentate arylazo backbone. The catalyst is compatible with both primary and secondary alcohols, yielding a wide variety of substituted aldazines, ketazines, and N-acylhydrazones in good isolated yields in air. Control experiments are conducted to elucidate the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Rakesh Mondal, Amit Kumar Guin, Gargi Chakraborty, Nanda D. Paul
Summary: Catalysis provides a simple way to prepare valuable molecules from readily available raw materials, mostly involving multi-electron transformations. Expensive heavy metal catalysts need to be replaced by affordable 3d metals for sustainable development. Metal-ligand cooperative approaches using transition metal complexes show promise in allowing interesting chemical transformations while using 3d metals for multi-electron transfers.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Siuli Das, Rakesh Mondal, Amit Kumar Guin, Nanda D. Paul
Summary: This study reports ligand-centered redox controlled Zn(II)-catalyzed multicomponent approaches for synthesizing pyrimidines and triazines. The well-defined Zn(II)-catalyst (1a) with redox-active ligand L-1a enables the preparation of substituted pyrimidines and triazines via dehydrogenative alcohol functionalization reactions, with good tolerance towards a wide range of substrates. The active participation of ligand-centered redox events allows the Zn(II)-complex 1a to efficiently act as a catalyst for synthesizing these N-heterocycles, with electron transfer processes occurring at the azo-aromatic ligand during the catalytic reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Amit Kumar Guin, Rakesh Mondal, Gargi Chakraborty, Subhasree Pal, Nanda D. Paul
Summary: In this study, the synthesis and characterization of two ruthenium-based pincer-type catalysts were reported. These catalysts were used in the synthesis of substituted pyrroles through dehydrogenative alcohol functionalization reactions. A comparison between the catalytic activities of the two catalysts was made to understand the advantages and disadvantages of the metal-ligand cooperative approach.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Suman Sinha, E. Muhammed Sahad, Rakesh Mondal, Siuli Das, Litty Thomas Manamel, Paula Brandao, Bas de Bruin, Bikas C. Das, Nanda D. Paul
Summary: In this study, a ligand-centered redox-controlled strategy was used to synthesize an unusual binuclear diradical cobalt(III) complex. The complex showed promising potential for application as a molecular memory device.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Subhajit Chakraborty, Rakesh Mondal, Subhasree Pal, Amit Kumar Guin, Lisa Roy, Nanda D. Paul
Summary: We developed a sustainable and eco-friendly method for selective N-alkylation of various amines using a well-defined Zn(II)-catalyst with a tridentate arylazo scaffold. A total of 57 N-alkylated amines were synthesized with good to excellent yields, including 17 new examples. The Zn(II)-catalyst demonstrated wide functional group tolerance and compatibility for the synthesis of dialkylated amines, providing high yields for the precursors of tripelennamine and thonzonium bromide drugs.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Subhasree Pal, Siuli Das, Subhajit Chakraborty, Subhankar Khanra, Nanda D. Paul
Summary: In this study, a Zn(II)-catalyzed solvent-free sustainable synthesis of tri- and tetra-substituted pyridines was reported. The primary feedstock used was alcohols and NH4OAc served as the nitrogen source. The well-defined air-stable Zn(II)-catalyst, featuring a redox-active tridentate azo-aromatic pincer, was used for the synthesis of a wide variety of unsymmetrical 2,4,6-substituted pyridines by three-component coupling of alcohols with NH4OAc. The reactions proceeded efficiently and produced high yields of the desired products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Amit Kumar Guin, Subhasree Pal, Subhajit Chakraborty, Santana Chakraborty, Nanda D. Paul
Summary: A Ru(II)-catalyzed N-alkylation reaction of amines with C1-C10 aliphatic alcohols was described. The air-stable catalyst 1a exhibited wide functional group tolerance and high catalytic efficiency, requiring only low catalyst loading. Various N-methylated, N-ethylated, and N-alkylated amines were efficiently prepared. The reaction proceeded through a borrowing hydrogen transfer pathway and showed excellent chemo-selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Sucheta Mondal, Subhasree Pal, Subhankar Khanra, Santana Chakraborty, Nanda D. Paul
Summary: Herein, a cobalt-catalyzed sustainable approach for C-N cross-coupling reaction between amines and alcohols is reported. The well-defined Co-catalyst 1 a with a 2-(phenyldiazenyl)-1,10-phenanthroline ligand efficiently alkylates diamines producing N,N'-dialkylated amines and shows excellent chemoselectivity. This catalyst is also compatible with synthesizing N-heterocycles via dehydrogenative coupling of amines and alcohols.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Gargi Chakraborty, Rakesh Mondal, Amit Kumar Guin, Nanda D. Paul
Summary: In this study, a nickel-catalyzed sustainable synthesis method was utilized to prepare a variety of five-membered fused nitrogen heterocycles, including benzimidazole, purine, benzothiazole, and benzoxazole. This was achieved through acceptorless dehydrogenative functionalization of alcohols and borrowing hydrogen approach, using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst. Control experiments were conducted to elucidate the reaction mechanism.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
