Article
Chemistry, Applied
Hao Li, Hui Luo, Yan Ban, Yan Wang, Dianjun Li, Jinhui Yang
Summary: This paper describes a thioamide-chelation-assisted direct C-H activation method for the vinylation and arylation of ferrocenes under mild and base-free conditions catalyzed by Rh(III) and Ir(III) respectively. Various monovinyl and monoaryl substituted thioamideferrocenes were obtained with high yields using a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Jiang Wang, Pinzhuo Ren, Gongping Gu, Zongyou Jiang, Bolin Xiang, Shi Tang, Ai-Qun Jia
Summary: An efficient and convenient method for the construction of diverse free (N-H)-benzazepinoindoles using Pd-catalyzed C(sp(2))-H imidoylative cyclization of 3-(2-isocyanobenzyl)-1H-indoles was developed. The reaction displays a broad substrate scope and can be scaled up, providing a practical route to valuable bioactive azepinoindoles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sylvain Bertho, Radhouan Maazaoui, Damla Torun, Ismael Dondasse, Raoudha Abderrahim, Cyril Nicolas, Isabelle Gillaizeau
Summary: An attractive and cost-effective alternative approach using FeCl2 or non-toxic iron powder was developed for the beta-C(sp(2))-H (fluoro)alkylation of a range of cyclic and acyclic non-aromatic enamides, showing regioselectivity, broad substrate scope, and good functional group tolerance.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Peng Chen, Zhi-Yong Wang, Xiao-Shui Peng, Henry N. C. Wong
Summary: An efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners is presented. Over 30 examples were obtained with moderate to good yields and high stereo-selectivities. The practicality of this method is evidenced by a gramscale synthesis, and a preliminary mechanistic investigation was also performed.
Article
Chemistry, Organic
Muniyappa Vijaykumar, Benudhar Punji
Summary: The palladium-catalyzed chemoselective C(sp(2))-H and C(sp(3))-H acetoxylation of synthetically useful tertiary amides is reported under relatively mild reaction conditions. The reaction proceeds through the assistance of a weakly coordinated directing group and requires low catalyst loading. Diverse functionalities can be tolerated under the reaction conditions, and further functionalization to alcohols, alcohol-acids, and tertiary amines is demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daeun Kim, Geunho Choi, Weonjeong Kim, Dongwook Kim, Youn K. Kang, Soon Hyeok Hong
Summary: The site-selectivity of Pd-catalyzed direct C-H arylation reaction of simple arenes is influenced by the electronic properties of the arenes, with electron-rich arenes preferring meta-arylation and electron-deficient arenes preferring ortho-arylation. Mechanistic investigations revealed that the reaction operates through a cooperative bimetallic mechanism rather than the originally proposed monometallic CMD mechanism, with the transmetalation step suggested as the selectivity-determining step.
Article
Chemistry, Organic
Writhabrata Sarkar, Aniket Mishra, Arup Bhowmik, Indubhusan Deb
Summary: A copper-catalyzed method has been developed for the direct intermolecular ortho-silylation of benzamides, providing organosilane products in moderate to high yields. This method is operationally simple, tolerates a wide range of functional groups, and has been demonstrated to be practical and effective on a gram-scale experiment for constructing C-Si bonds in synthetic organic chemistry.
Article
Chemistry, Organic
Chaoyu Zhao, Siwei Yang, Yaxuan Cheng, Ruxin Qu, Xuri Huang, Huiling Liu
Summary: DFT calculations were used to investigate the mechanism of Pd(II)-catalyzed late-stage nondirected C(sp(2))-H cyanation of toluene. The results showed that the morphology of the active species is crucial for the observed metalation/deprotonation step and regioselectivity. Interestingly, transmetalation was identified as the rate-determining and turnover-determining step with the largest overall change in free energy.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Saori Tsuzuki, Shunya Sakurai, Akira Matsumoto, Taichi Kano, Keiji Maruoka
Summary: This study describes a Ni-catalyzed direct C-H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors. The reaction forms a new C(sp(3))-C(sp(2)) bond via selective cleavage of both C(sp(3))-C(sp(3)) and C(sp(2))-H bonds. Due to the structural diversity of alkylsilyl peroxides, a wide range of alkyl chains including functional groups and complex structures can be introduced at the ortho-position of readily available N-quinolylbenzamide derivatives.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Biswajit Mondal, Prasanjit Ghosh, MrinalKanti Kundu, Sajal Das
Summary: In this study, a novel method was developed for regioselective ortho-C(sp(2))-H arylation in aqueous medium using 8-AIP as a promising and removable bidentate directing group/auxiliary. The protocol demonstrated excellent functional group tolerance and exclusive site-selectivity, providing a rapid route to a library of unsymmetrical amides in good to excellent yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Manish K. Gupta, Chinmay K. Jena, Nagendra K. Sharma
Summary: The paper describes the synthesis of N-alkyl-3-methenyl chiral isoindolinone derivatives from aryl amides of l-amino acids and non-activated alkene via Pd-catalyzed C(sp(2))-H olefination. The amino acid residue acts as a directing group for olefination at the aryl ring and cyclization occurs at the amide NH. This methodology could be useful in transforming standard amino acids into respective chiral isoindolinone derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Raghunath Bag, Nagendra K. Sharma
Summary: This study presents a convenient synthetic method for the Pd-catalyzed picolinamide-directed site-selective C(sp(2))-H chalcogenation of alpha-amino acids and peptides. It has been successfully applied to the synthesis of a variety of alpha-amino acids, benzylamines, and phenethyl amines with moderate to good yields and good selectivity. Moreover, it allows for late-stage peptide chalcogenation and offers wide substrate scopes and various postsynthetic utilities.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Manish K. K. Gupta, Ankita Panda, Subhasish Panda, Nagendra K. K. Sharma
Summary: Isoindolinone is a constituent of natural products with various bioactivities. A synthetic methodology for introducing isoindolinone residues to peptides has been developed, and the conformational changes caused by the isoindolinone scaffold have been demonstrated. Isoindolinonyl peptides offer a pathway for the synthesis of novel foldamers and therapeutic agents.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Subhashree. S. S. Panda, Nagendra. K. K. Sharma
Summary: This report describes a new synthetic methodology for the ortho-arylation of arylamines and alpha-aromatic amino acids using a Pd-catalyzed C(sp(2))-H activation. The use of diethoxyethyl-l-proline as a transient directing group allows for the formation of mono-arylated arylamines as the major products using aryliodides. This method shows promise for the synthesis of various biphenyl amines and novel peptidomimetics.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Liang Jin, Peng Zhang, Ya Li, Xin Yu, Bing-Feng Shi
Summary: Efficient synthesis of axially chiral styrenes with high enantioselectivity was achieved using a Pd(II)-catalyzed thioether-directed alkenyl C-H olefination strategy. The reaction showed ease of operation, mild conditions, high functional group tolerance, complete Z-selectivity, and excellent enantioselectivities, with potential for scaling up and further derivatization into chiral sulfoxide ligands.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Rajesh Malhotra, Chhanda Rarhi, K. V. Diveshkumar, Rajib Barik, Ruhee D'cunha, Pranab Dhar, Mrinalkanti Kundu, Subrata Chattopadhyay, Subho Roy, Sourav Basu, P. I. Pradeepkumar, Saumen Hajra
BIOORGANIC & MEDICINAL CHEMISTRY
(2016)
Article
Chemistry, Inorganic & Nuclear
Chandan K. Mahato, Mrinalkanti Kundu, Animesh Pramanik
TETRAHEDRON-ASYMMETRY
(2017)
Article
Chemistry, Multidisciplinary
Rajesh Malhotra, Chhanda Rarhi, K. V. Diveshkumar, P. Bommisetti, Sushree Prangya P. Pany, Subho Roy, P. I. Pradeepkumar, Mrinalkanti Kundu
Article
Chemistry, Organic
Tanmay K. Pati, Sudipto Debnath, Mrinalkanti Kundu, Uttam Khamrai, Dilip K. Maiti
Article
Chemistry, Organic
Chandan K. Mahato, Sayan Mukherjee, Mrinalkanti Kundu, Animesh Pramanik
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Arijit Das, Arup Maiti, Mrinalkanti Kundu, Kuldeep K. Roy, Inul Ansary
SYNTHESIS-STUTTGART
(2019)
Article
Chemistry, Multidisciplinary
Ashis Roy, Mrinalkanti Kundu, Pranab Dhar, Arnish Chakraborty, Soumen Mukherjee, Jayatri Naskar, Chhanda Rarhi, Rajib Barik, Susanta Kumar Mondal, Mushtaq Ahmad Wani, Rahul Gajbhiye, Kuldeep K. Roy, Arup Maiti, Priyadarshi Manna, Susanta Adhikari
Article
Chemistry, Organic
Tanmay K. Pati, Sk Ajarul, Mrinalkanti Kundu, Deepak Tayde, Uttam Khamrai, Dilip K. Maiti
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Chandan K. Mahato, Sayan Mukherjee, Mrinalkanti Kundu, Virbhadra P. Vallapure, Animesh Pramanik
Summary: This study utilized a new set of organic catalysts for asymmetric Michael reactions in water, achieving high efficiency and yield, offering a new method for green synthesis. The strategy also successfully synthesized an optically active octahydroindole, a key component found in many natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Ashis Roy, Tonmoy Sarkar, Sebak Datta, Arup Maiti, Monali Chakrabarti, Trisha Mondal, Chaitali Mondal, Apurba Banerjee, Subhasis Roy, Soumen Mukherjee, Pragati Muley, Sabyasachi Chakraborty, Manish Banerjee, Mrinalkanti Kundu, Kuldeep K. Roy
Summary: A potent and orally bioavailable inhibitor (compound 1) of extracellular secreted enzyme autotaxin (ATX) was developed through structure-based design, synthesis, and biological investigations. Compound 1 exhibited strong ATX inhibitory activity in vitro, along with favorable pharmacokinetic properties and oral availability, indicating its potential for in vivo experiments.
CHEMICAL BIOLOGY & DRUG DESIGN
(2022)
Article
Chemistry, Organic
Tapas Kumar Das, Mrinalkanti Kundu, Biswajit Mondal, Prasanjit Ghosh, Sajal Das
Summary: A unique N,O-bidentate ligand catalyzed direct arylation of unactivated arenes to synthesize (Het)biaryl scaffolds efficiently under UV-irradiation at room temperature. The method showed good functional group tolerance and synthetic pathway, with potential applications in biological research.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Mrinalkanti Kundu, Aditi Dutta, Kuldeep K. Roy, Sajal K. Mal, Shouvik Karmakar, Aritra Mandal, Susanta K. Mondal, Sanjay Kumar, Soumya Saha, Subhankar Pradhan, Ratul Sarkar, Monali Chakrabarti, Pradip K. Malik, Manish Banerjee
Summary: Malaria remains a significant public health problem, and the emergence and spread of resistance to artemisinin-based combination therapies pose a threat. Researchers have used docking studies and pharmacokinetic studies to identify a potential new imidazopyridine compound with anti-malarial activity. In vitro and in vivo experiments have shown promising results for this compound.
CHEMICAL BIOLOGY & DRUG DESIGN
(2023)
Article
Chemistry, Organic
Priyadarshi Manna, Mrinalkanti Kundu, Ashis Roy, Susanta Adhikari
Summary: The synthesis of deuterium-labeled organic compounds is increasingly important, especially after the approval of deutetrabenazine by the Food and Drug Administration. Metal-catalyzed deuterium labeling methods are unique and have proven to be powerful additions in different areas of chemical science.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Biswajit Mondal, Prasanjit Ghosh, MrinalKanti Kundu, Tapas Kumar Das, Sajal Das
Summary: In this study, the palladium-catalyzed arylation of the inert beta-C(sp(2))-H bond of carboxylic acid derivatives is reported for the first time, using 8-aminoimidazo[1,2-a]pyridine (AIP) as a novel removable directing group. The protocol is scalable, exhibits high levels of beta-site selectivity, and tolerates a broad spectrum of functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)