Article
Chemistry, Organic
Xianjun Xu, Huangdi Feng, Erik V. Van der Eycken
Summary: An efficient synthesis route for unsymmetric 1,4-diamino-2-butynes has been developed using a microwave-assisted Cu(I)-catalyzed cross-A(3)-coupling/decarboxylative coupling process. The multicomponent reaction yields target products in moderate to good yields with high chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Weiyou Zhou, Anwei Wang, Zhenji Kong, Xiaoting Tian, Zhenzhen Xia, Zhihui Zhang, Mingyang He, Qun Chen, Shixin Sun
Summary: A convenient catalytic protocol using CuCoFe layered double hydroxide (LDH) for efficiently constructing indoline-fused tetrahydroisoquinolines has been described. The research offers a unique opportunity to develop a synthetic methodology for N-containing polycyclic compounds.
Article
Chemistry, Physical
Silver Nyambo, Yuchen Zhang, Dong-Sheng Yang
Summary: Metal-mediated N-H and C-H bond activation of aliphatic amines is an effective strategy for synthesizing biologically important molecules. This study focused on Ln (Ln = La and Ce) atom reactions with dimethylamine, analyzing the formation and characteristics of metallaaziridines through experimental and theoretical approaches. The results provide insights into the mechanism of formation of these three-membered metallacycles and their potential applications in organic synthesis.
JOURNAL OF CHEMICAL PHYSICS
(2021)
Article
Chemistry, Organic
Ahmad Reza Moosavi-Zare, Mohammad Rezaei-Gohar, Mahsa Tavasoli, Hamid Goudarziafshar
Summary: N-Sulfopyridin-1-ium monozinc(II) trichloride ([NSPy]ZnCl3) was prepared and used as a multipurpose catalyst for the synthesis of propargylamines by the A(3) coupling reaction of aromatic aldehydes, alkynes, and secondary amines under mild conditions. The carbonyl group in the aldehyde was activated by the acidic part in the catalyst, while zinc was responsible for the C-H activation of phenylacetylene.
Article
Chemistry, Organic
Xin-Wei Guo, Li-Xia Quan, Xian-Hong Zhu, Fa-Yun Chen, An-Xi Zhou, Liu-Liang Mao, Jie-Ping Wan, Shang-Dong Yang
Summary: The aluminum(iii) triflate catalyzed three-component coupling reaction allows for the synthesis of phosphoryl quinoline derivatives in a simple system without the need for transition metals, ligands, or additives, making it suitable for the rapid preparation of a variety of new potential N-P bidentate ligands.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ashmita Singh, Anudeep Kumar Narula
Summary: A new methodology was developed for the synthesis of propargylamines via A(3) coupling reaction. The reaction showed high yield, shorter reaction duration, and operated smoothly in air without any metal catalyst.
RESULTS IN CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sumit Das, Shantonu Roy, Arup Bhowmik, Writhabrata Sarkar, Imtiaj Mondal, Aniket Mishra, Shubhra Jyoti Saha, Sudip Karmakar, Indubhusan Deb
Summary: This study establishes a straightforward strategy for the direct incorporation of sulfonyl units into a xanthene moiety, yielding xanthen-9-sulfone derivatives in good to excellent yields via metal-free radical-radical cross-coupling reaction. The methodology uses easily accessible starting materials and proceeds efficiently under simple reaction conditions with a high degree of functional group compatibility.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Lei Yang, Maolin Sun, Liming Cao, Chaoming Liang, Jiasheng Yang, Junjun Yi, Ruihua Cheng, Yueyue Ma, Jinxing Ye
Summary: A three-component reductive coupling reaction has been developed under electrochemical conditions, involving aldehydes, amines, and cyanopyridines. In situ generation of imine and cyanopyridine allows for simultaneous single-electron reduction at the cathode, leading to the formation of diarylmethylamines through radical coupling. This method enables the modular synthesis of various secondary and tertiary amines with broad functional group compatibility.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Meng-Hui Li, Xiao-Ju Si, He Zhang, Dandan Yang, Jun-Long Niu, Mao-Ping Song
Summary: An efficient cobalt-catalyzed three-component coupling reaction is disclosed, which can construct C(sp(2))-C(sp(3)) and C-O bonds in one-pot with high yields and functional group compatibility. Mechanistic studies suggest a radical process may be involved in the reaction.
Article
Chemistry, Multidisciplinary
Fabian Dankert, Jan-Erik Siewert, Priyanka Gupta, Florian Weigend, Christian Hering-Junghans
Summary: The translation introduces the source of N-containing molecules and the methods for their activation, including ammonia activation by single transition metal centers and low-valent main group species, as well as the stabilization of mono-valent phosphorus species by phosphines. DFT studies reveal that the exchange between NH3 and PMe3 requires the concerted action of two NH3 molecules. Furthermore, the activation of H2NR and HNR2 is demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yi-Fan Zhang, Han-Nan Chen, Yi Xiao, Zhencun Cui, Wei David Wang, Guo-Qiang Xu
Summary: Here, a novel protocol for synthesizing alpha-functionalized saturated aza-heterocycles is presented, allowing for the easy installation of various nucleophilic groups. Additionally, a range of biologically valuable 3,3'-diindolylmethane derivatives can be readily synthesized under mild photocatalytic conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Ran Fang, Lin Zhou, Alexander M. Kirillov, Lizi Yang
Summary: The DFT study investigated a zirconium-catalyzed hydroaminoalkylation reaction, revealing the electrophilic nature of the substrates and the nucleophilic behavior of the zirconaaziridine catalyst. The distortion/interaction analysis showed how distortion and interaction energies control regioselectivity and diastereoselectivity with different alkene substrates. These findings offer insights into the substrate-dependent product selectivity in the reaction.
Article
Chemistry, Organic
Kai Xu, Zhenli Xu, Mengzhen Zhang, Xiaoxiao Yan, Guoliang Mao, Tao Wang, Yangjie Wu, Lantao Liu
Summary: The efficient aerobic oxidative hydroxysulfurization reaction developed in this study allows for the production of alpha,alpha-difluoro-beta-hydroxysulfides from gem-difluoroalkenes and aryl or alkyl thiols, demonstrating high levels of chemoselectivity and regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Aniket Gupta, Anusuya Saha, Ajijur Rahaman, Jogendra Kumar, Eringathodi Suresh, Bishwajit Ganguly, Sukalyan Bhadra
Summary: A monoprotected amino acid Bz-Gly-OH is found to assist in the asymmetric allylic alkylation reaction by enaminepalladium catalysis, attacking the pi-allylpalladium complex through an outer sphere mechanism. This discovery potentially offers a new mode of bifunctional catalysis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Aniket Gupta, Anusuya Saha, Ajijur Rahaman, Jogendra Kumar, Eringathodi Suresh, Bishwajit Ganguly, Sukalyan Bhadra
Summary: A monoprotected amino acid Bz-Gly-OH plays a assisting role in the allylic alkylation of various compounds during enamine-palladium catalysis. Density functional theory calculations suggest that Bz-Gly-OH assists in the formation of an enamine which attacks the pi-allylpalladium complex through an outer sphere mechanism. The preliminary result indicates an asymmetric allylic alkylation under a new mode of bifunctional catalysis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
S. Ravindra, Abinash Nayak, C. P. Irfana Jesin, Ganesh Chandra Nandi
Summary: A visible-light promoted dual catalytic method utilizing cobalt and photoredox catalysts has been developed for the direct synthesis of sulfonimidoyl guanidine via a three-component reaction. The protocol is fast, mild, and provides a wide range of products in yields of 56-86%. Additionally, the study reports the formation of sulfonimidoyl isourea and sulfonimidoyl isothiourea using alcohol and thiol as nucleophiles, respectively, which have not been reported in the literature.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
V. R. Padma Priya, C. P. Irfana Jesin, Ganesh Chandra Nandi
Summary: A transition-metal-free method for the synthesis of N-(o-halo)arylsulfoximines/sulfonimidamides via the reaction of aryne precursor and CCl4/CBr4 in the presence of KF/18-crown-6 has been developed. The protocol shows good substrate scope and the regioisomers formed from unsymmetric aryne precursor can be effectively separated by column chromatography.
Article
Medicine, Research & Experimental
Mamata Singh, Virendra Singh, Tushar S. Basu Baul, Biplob Koch
Summary: The study demonstrated that TSD-30-F and TSD-34-F micelles have significant apoptotic induction effects on breast cancer cells by regulating the expression of specific genes and proteins. In addition, in silico analysis showed efficient binding affinity of the micelles with key proteins involved in apoptosis.
Article
Chemistry, Organic
Dhananjay Yadav, Maya Shankar Singh
Summary: A simple and efficient cascade approach for the synthesis of a series of 1,3-thiazinanes has been developed using beta-ketothioamide and epichlorohydrin in an intermolecular [3+3] heteroannulative coupling. This method offers several advantages, such as avoiding potential toxicity, easy work-up, and high yields, and it can be performed using readily available starting materials under transition-metal-free conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shahnawaz Khan, Monish Arbaz Ansari, Maya Shankar Singh
Summary: This study presents a chemo- and regioselective cascade annulation between fi-ketothioamides and diazo-substituted hypervalent iodine reagents under transition-metal-free and base-free conditions at room temperature. A divergent construction of fused-heterocyclic scaffold thiazolothiadiazoles has been achieved with the advantages of operational simplicity, scalability, broad substrate compatibility, and mild reaction conditions. This one-pot strategy not only avoids potential toxicity but also broadens the arsenal of synthetic methods to obtain fused N,S-heterocyclic frameworks.
Article
Chemistry, Organic
Ravindra Sundaresan, Shivam Kumar Dubey, Ramesh Kataria, Ganesh Chandra Nandi
Summary: An efficient, mild, and novel route for synthesizing sulfonylurea via nickel-catalyzed tandem coupling of sulfonyl azide, isocyanide, and water in aqueous media is presented. Sulfonyl azide acts as a nitrene precursor, reacting with isocyanide to generate carbodiimide. Water then acts as a nucleophile, reacting with carbodiimide to yield the product. The protocol utilizes an inexpensive nickel catalyst, environmentally friendly water (as the nucleophile), and operates at room temperature, providing moderate to good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Pragya Pali, Maya Shankar Singh
Summary: A simple and efficient domino strategy was developed for the synthesis of 1,2-dithioles using easily accessible dithioesters and aryl isothiocyanates. The reaction proceeded smoothly at room temperature without the need for a catalyst or additive, and produced high yields of 1,2-dithioles with diverse functional groups. The use of cheap and readily available reagents, O-2 as a green oxidant, and the ability for gram-scale synthesis are notable features of this approach. The formation of S-S bonds and cascade ring construction in this reaction were found to proceed through a radical pathway.
Article
Chemistry, Organic
V. R. Padma Priya, A. Antony Haritha Mercy, K. Natarajan, Ganesh Chandra Nandi
Summary: Sulfoximines are used as S-aryl surrogates to prepare 3-arylsulfenylindoles by reacting with indoles in the presence of I-2 under visible-light irradiation. This environmentally friendly method is fast, mild, and does not require any metal, photocatalyst, additive, or oxidant. It provides moderate to good yields and has a wide substrate scope.
Article
Chemistry, Applied
Anup Kumar Yadav, Vipin Kumar, Pragya Pali, Subhasish Ray, Abhineet Verma, Maya Shankar Singh
Summary: Here, a one-pot viable protocol for synthesizing tetrasubstituted 2-aminothiophenes using readily accessible α-enolic dithioesters and abundant fumaronitrile under transition metal-free conditions at room temperature in open air is reported. The reaction proceeds via successive Michael-type addition/intramolecular cyclization/isomerization cascades. The added features of this protocol include benign conditions, exclusive regio- and chemoselectivity, excellent atom-/step-economy, easy purification, and tolerance of a wide range of functional groups. It not only provides a robust and modular approach to various 2-aminothiophenes, but also demonstrates the potential of dithioesters and fumaronitrile in intermolecular cross-coupling reactions, expanding the arsenal of synthetic methods.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Sundaresan Ravindra, Kannan Natarajan, Vetrivel R. Padma Priya, Ramesh Kataria, Ganesh Chandra Nandi
Summary: We report an efficient protocol for the synthesis of sulfonyl carbamimidic azide and sulfonyl aminotetrazole via Co-catalyzed three component coupling under visible light at room temperature. The sulfonyl carbamimidic azide cyclizes in the presence of base to deliver N-sulfonyl aminotetrazole, which can also be synthesized directly without isolating the sulfonyl carbamimidic azide.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Arivalagan Shabashini, Sathiaraj Richard, Sumit Kumar Panja, Ganesh Chandra Nandi
Summary: Two tricyanopyrroline based NIR dyes (TCP-Tph and TCP-HyDe) with solvent-sensitive and reverse solvatochromic properties were developed. These dyes selectively detect fluoride ions among various anions, and the mechanistic study of interaction between the dye and fluoride ions was conducted. The dyes were successfully applied for real-time monitoring of fluoride ions in toothpaste and sewage water, and a cost-effective paper-based fluoride detection kit was also developed.
Article
Chemistry, Organic
Ravikumar Merneedi, Mamata Singh, Pradipta Sinha, Rajendra Anugula
Summary: The study presents a streamlined procedure for synthesizing bis(indolyl)methane derivatives using decanoic acid as a promoting medium. The method does not require workup and purification, avoids the use of metal-containing catalysts, and provides a simple, cost-effective procedure with excellent yield. It is suitable for large-scale synthesis and eliminates the use of corrosive acids.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ganesh Kumar, Subhasish Ray, Gaurav Shukla, Maya Shankar Singh
Summary: A one-pot synthesis of bench-stable quinoxaline N-oxides was achieved using a-oxoketene N,S-acetals and tert-butyl nitrite in open air. The double functionalization of N,S-acetals proceeds via an unexpected (Csp(2))-H nitrosation by NO radical and subsequent intramolecular N-arylation leading to quinoxaline, which is then oxidized to quinoxaline N-oxides. This protocol offers short reaction time, good functional group tolerance, and mild conditions without the need for a catalyst or external additive.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Subhasish Ray, Anup Kumar Yadav, Saurabh Singh, Monish Arbaz Ansari, Maya Shankar Singh
Summary: A one-pot electronically controlled [4 + 2] cycloaddition reaction between in situ generated benzyne and 2-arylidene-1-indenones has been discovered, allowing the construction of novel spirocyclic frameworks in a regio- and diastereoselective manner. This protocol offers simplicity, good functional group tolerance, and avoids the need for metal catalysts and external additives. The synthetic application of 2-arylidene-1-indenones has been extended, providing easy access to valuable 10'H-spiro[indene-2,9'-phenanthren]-1(3H)-ones in good yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
S. K. Abu Saleh, Atanu Hazra, Maya Shankar Singh, Saumen Hajra
Summary: The selective C3-allylation and formal [3 + 2]-annulation of spiro-aziridine oxindoles with allylsilanes can be catalyzed by Bronsted acid and/or Lewis acid, resulting in the formation of 3-allyl-3-aminomethyl oxindoles and 5-silyl methyl spiro[pyrrolidine-3,3'-oxindoles], respectively. Acid-catalyzed methods lack stereoselectivity when chiral spiroaziridines are used, but good stereoselectivity can be achieved through the reaction of nonracemic spiroaziridines with allyl-Grignard reagent under catalyst-free conditions. This allylation protocol is useful for the synthesis of biologically active compounds, such as coerulescine and various 5'-substituted spiro[pyrrolidine-3,3'-oxindoles].
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
