Article
Chemistry, Multidisciplinary
Tobias Michael Milzarek, Jerome Waser
Summary: The first trifluoromethylation of vinylbenziodoxolones (VBX) using bench-stable, high-valent copper(III) species is reported. The reaction can be initiated under thermal conditions and/or irradiation (365 nm) and leads to stereoselective formation of trifluoromethylated alkenes. Various VBX reagents derived from tyrosine, cysteine, small peptides, thiols, and amides can be used as precursors. The obtained alkenes can be further functionalized through reduction or epoxidation of the trifluoromethylated double bond. The method is suitable for large-scale batch/flow synthesis and can be conducted under visible light irradiation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Yang Yuan, Xiao-Feng Wu
Summary: A novel copper-catalyzed carbonylative trifluoromethylation of unactivated alkenes has been developed, allowing the preparation of a broad range of beta-trifluoromethylated carboxylic acid derivatives in moderate to excellent yields with excellent regioselectivity. It is worth noting that even the simplest olefin, ethylene gas, can be directly applied to obtain beta-trifluoromethylated amides and esters. This transformation represents the first example of carbonylative trifluoromethylation of alkenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
He-Ping Li, Xiang-Hong He, Cheng Peng, Jun-Long Li, Bo Han
Summary: This review summarizes the applications of late-stage functionalization strategies in the trifluoromethylation of natural products in the past ten years. These strategies include metal catalysis, organocatalysis, light-driven reactions, and electrochemical synthesis. The reaction models of each method are emphasized, along with the challenges, limitations, and future prospects of this approach.
NATURAL PRODUCT REPORTS
(2023)
Article
Chemistry, Multidisciplinary
Da Seul Lee, Vineet Kumar Soni, Seunga Heo, Ho Seong Hwang, Youngmin You, Eun Jin Cho
Summary: A sustainable method has been developed to synthesize highly functionalized CF3-hydroquinone derivatives, which exhibit potent biological activity. The approach involves photoirradiation of a mixture containing readily available benzoquinones and CF3SO2Na, resulting in the generation of CF3-hydroquinones through photoinduced charge-transfer reactions. This method is practical, atom-economical, and enables site-selective three-component trifluoromethylation in the presence of vinyl arenes.
Article
Chemistry, Organic
Zi-Qi Zhang, Yi-Hao Xu, Jing-Cheng Dai, Yan Li, Jie Sheng, Xi-Sheng Wang
Summary: A facile and efficient approach for the synthesis of CF3-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method demonstrates low catalyst loading, high regiocontrol, and broad scope under mild conditions, proving its versatility and potential for further derivatization.
Article
Chemistry, Organic
Wei Wu, Shunli Wen, Xinyu Zhang, Qi Lin, Zhiqiang Weng
Summary: A highly efficient and regioselective synthesis of highly substituted 2-trifluoromethyl pyrrole derivatives is reported via a silver-catalyzed cyclization of vinyl azides with ethyl 4,4,4-trifluoro-3-oxobutanoate. Various types of alpha-(heteo)aryl, alkyl, alpha-aryl, and alpha,beta-disubstituted vinyl azides can participate in this transformation. The proposed reaction mechanism involves the addition of in situ generated 2H-azirine to the diketone species, followed by intramolecular addition, N-C-1 cleavage, and elimination.
Article
Chemistry, Organic
Xiaowei Chen, Wenhui Wei, Chunyang Li, Hongwei Zhou, Baokun Qiao, Zhiyong Jiang
Summary: A modular strategy was reported for accessing remote fluoroalkylated azaarene derivatives and alpha-deuterated analogues, isosteres of many pharmaceutically important compounds. Transformations under sustainable photoredox catalysis platform efficiently yielded valuable products with high yields and substantial deuterium incorporation. The work demonstrated the viability of hydrogen atom transfer of the alpha-sp(3) C-H of electron-withdrawing azaarenes with alkyl radicals.
Article
Chemistry, Multidisciplinary
Kingshuk Mahanty, Suman Kumar Saha, Atreyee Halder, Suman De Sarkar
Summary: The developed methodology presents an eco-friendly approach for electro-oxidative CF3-radical generation, leading to the synthesis of a beta,gamma-unsaturated oxime and subsequent cascade cyclization to form an isoxazoline scaffold. This method offers mild, robust, and scalable reaction conditions and has a wide range of substrate applicability. Mechanistic studies demonstrate the importance of anodic oxidation for the cascade process. Further conversion of the isoxazoline provides valuable derivatives.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Yilin Zhao, Xue Wang, Ru Yao, Chengwen Li, Zelin Xu, Liming Zhang, Guifang Han, Jingli Hou, Yangping Liu, Yuguang Song
Summary: In the presence of Fe(III) complex and Bipy ligand, CF3-containing spirocarbocycles were conveniently obtained in high yields (20-99%) with high regioselectivity through Iron-catalyzed trifluoromethylation of unactivated alkenes coupled with phenol dearomatizing spirocyclization.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Polina A. Petrova, Denis Sudarikov, Larisa L. Frolova, Roman Rumyantcev, Svetlana A. Rubtsova, Aleksandr Kutchin
Summary: Monoterpene trifluoromethylated compounds were synthesized for the first time with high yields. The reaction proceeded selectively at the C=O bond and the resulting compounds were further reduced to alpha-trifluoromethyl-beta-amino alcohols. Structure and configuration of the compounds were established.
Article
Chemistry, Organic
Wanqiao Huang, Cong Xu, Jianxin Yu, Mang Wang
Summary: An effective method for the aminotrifluoromethylation of alkenes was developed by using PhICF3Cl and ZnI2 as catalysts. The mechanism studies showed that the reaction involves an iodine anion-catalyzed radical chlorotrifluoromethylation of alkenes and a Lewis acid-promoted aminocyclization of the resulting chlorotrifluoromethylated intermediates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jing Qi, Jinhui Xu, Hwee Ting Ang, Bingbing Wang, Nipun Kumar Gupta, Srinivas Reddy Dubbaka, Patrick O'Neill, Xianwen Mao, Yanwei Lum, Jie Wu
Summary: In this study, a novel electrophotochemical approach is presented for the selective trifluoromethylation of (hetero)-arenes using trifluoroacetic acid (TFA) as the CF3 source. The method offers sustainable and environmentally-friendly synthesis of CF3-, CF2H-, and perfluoroalkyl-containing (hetero)-arenes with improved chemoselectivity by light irradiation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Pai Zheng, Chuan Liu, Qianding Zeng, Yi Zhang, Ying Liu, Jingjing He, Yupian Deng, Song Cao
Summary: A mild and practical Fe-catalyzed hydroxytrifluoromethylation of alpha-(trifluoromethyl)styrenes with CF3SO2Na in the presence of K2S2O8 and air has been developed. The reaction proceeds efficiently at room temperature without beta-fluoride elimination, resulting in good to excellent yields of alpha, beta-bistrifluoromethyl tertiary alcohols.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chen Fu, Zhaosheng Zhang, Yuzhen Li, Dongni Gao, Zi-Ning Cui, Zhaodong Li
Summary: We reported a versatile and efficient method for the synthesis of diverse fluoroalkylated amines. This photoinduced palladium-catalyzed cross coupling reaction of 1,3-dienes, amines, and fluoroalkyl iodides is controlled by the fluoroalkyl iodides, exhibiting excellent 3,4- and 1,4-selectivity. The method has a broad substrate scope, good functional group tolerance, and can be used for the late-stage modification of bioactive molecules.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xiang Chen, Jun Jiang, Xiao-Jun Huang, Wei-Min He
Summary: An electrochemical oxidative strategy for the synthesis of benzoxazines without transition-metal catalysts and external oxidants is described. Olefinic amides can be transferred to difluoromethylated benzoxazines with up to 87% yield via oxydifluoromethylation using CF2HSO2Na as the reagent in an undivided cell.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Aditya Upadhyay, Bhagat Singh Bhakuni, Rahul Meena, Sangit Kumar
Summary: The study investigates the introduction of organoselenium substituents at ortho-positions of phenols and explores the impact of different functionalities on their activities. This reaction enables the synthesis of novel selenium-containing compounds with potential radical quenching and antioxidant properties.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Aditya Upadhyay, K. Saurav, Evelin Lilly Varghese, Ananda S. Hodage, Amit Paul, Mahendra Kumar Awasthi, Sanjay Kumar Singh, Sangit Kumar
Summary: This article reports the synthesis and structural characterization of a bimetallic zinc selenolate complex that acts as a homogeneous catalyst for the electrochemical reduction of protons into hydrogen gas. The catalyst exhibits a high turnover frequency and stable performance under cathodic and anodic potentials, achieving a remarkable faradaic efficiency for the generation of hydrogen gas.
Article
Chemistry, Inorganic & Nuclear
Saravanan Raju, Harkesh B. Singh, Sangit Kumar
Summary: The synthesis and coordination behavior of a tetradentate organotelluroether ligand with copper and silver salts have been investigated. The ligand and metal complexes were characterized through various spectroscopic techniques and calculations. The study revealed the formation of self-assembled bimetallic complexes and the bridging role of metal ions in the formation of metallamacrocycles. The analysis also revealed a weak intramolecular interaction between the tellurium atoms. NBO calculations suggested that the tellurium atom has a higher electron donating ability than the quinoline nitrogen in the complexes.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Meeting Abstract
Hematology
Cristiana O'Brien, Tianyi Ling, Jacob Berman, Rachel Culp-Hill, Julie A. Reisz, Vincent Rondeau, Soheil Jahangiri, Jonathan St-Germain, Vinitha Macwan, Audrey Astori, Andy G. X. Zeng, Jun Young Hong, Meng Li, Min Yang, Sadhan Jana, John E. Dick, Hening Lin, Ari Melnick, Anastasia N. Tikhonova, Andrea Arruda, Mark D. Minden, Brian Raught, Angelo D'Alessandro, Courtney L. Jones
Article
Chemistry, Inorganic & Nuclear
Aditya Upadhyay, Kanika, Yogesh Mandhar, Monojit Batabyal, Saravanan Raju, Svastik Jaiswal, Ray J. Butcher, Sangit Kumar
Summary: In this study, a series of cobalt(ii) phenolate selenoether complexes were synthesized and characterized for their electrocatalytic hydrogen evolution reaction. The synthesized complexes exhibited enhanced stability and catalytic activity, and the mechanism of the hydrogen evolution reaction was revealed.
DALTON TRANSACTIONS
(2022)
Article
Astronomy & Astrophysics
Mostafizur Rahman, Shailesh Kumar, Arpan Bhattacharyya
Summary: The field of gravitational waves is advancing rapidly with the progress in gravitational-wave detectors, allowing for the detection of binary black hole mergers. This article focuses on an extreme mass-ratio inspiral (EMRI) system with a spherically symmetric static braneworld black hole that carries a tidal charge. The study estimates the impact of the tidal charge on gravitational wave flux and orbital phase, highlighting the potential observational implications in EMRI waveforms.
JOURNAL OF COSMOLOGY AND ASTROPARTICLE PHYSICS
(2023)
Article
Chemistry, Multidisciplinary
Raviraj Ananda Thorat, Yogesh Mandhar, Devendra Parganiha, Khushbu Bindesh Patil, Vikram Singh, Batul Shakir, Saravanan Raju, Sangit Kumar
Summary: The reaction of chiral 2-iodoferrocenecarboxamide, palladium(II) acetate, and triphenylphosphine ligand in acetonitrile resulted in the formation of an air-stable chiral (S-p)-2-(N,N-diisopropyl ferrocenecarboxamide) triphenylphosphine palladium(II) iodide complex. The isolated chiral palladium complex was characterized by various spectroscopic techniques and X-ray crystallography, revealing its structural and electronic properties. Furthermore, the synthesized chiral palladium complex exhibited catalytic activity in Suzuki-Miyaura coupling, Tsuji-Trost coupling, and phosphonation reactions.
Article
Chemistry, Medicinal
Pritiranjan Sahoo, Dipti Ranjan Lenka, Monojit Batabyal, Pritam Kumar Pain, Sangit Kumar, Debasish Manna, Atul Kumar
Summary: This study synthesized various ebselen derivatives and investigated their interaction mechanism with SARS-CoV-2 main protease (M-pro). It was found that the introduction of an electron-withdrawing group improved the inhibition efficacy, and the structures of the inhibited M-pro and catalytically inactive mutant were solved.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2022)
Article
Biochemistry & Molecular Biology
Ananya Anmangandla, Sadhan Jana, Kewen Peng, Shamar D. Wallace, Saket R. Bagde, Bryon S. Drown, Jiashu Xu, Paul J. Hergenrother, J. Christopher Fromme, Hening Lin
Summary: Researchers have developed a robust fluorescence polarization assay for various viral and human macrodomains, including SARS-CoV-2 Macro1, using a novel tracer TAMRA-ADPr. The assay identified GS441524 as a highly selective inhibitor of SARS-CoV-2 Macro1 over other macrodomains.
ACS CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Saket Jain, Monojit Batabyal, Raviraj Ananda Thorat, Pratibha Choudhary, Raushan Kumar Jha, Sangit Kumar
Summary: Efficient synthesis of 2-phenyl-benzamide tellurenyl iodides was achieved by inserting a tellurium atom into the carbon-iodine bond of 2-iodobenzamides. These compounds were found to be effective catalysts for the activation of epoxide with CO2 for the synthesis of cyclic carbonates and the formation of 1,3-diaryl ureas from anilines and CO2. Mechanistic investigations revealed the formation of a catalytically active Te-N heterocycle intermediate.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Hematology
Cristiana O'Brien, Tianyi Ling, Jacob M. Berman, Rachel Culp-Hill, Julie A. Reisz, Vincent Rondeau, Soheil Jahangiri, Jonathan St-Germain, Vinitha Macwan, Audrey Astori, Andy Zeng, Jun Young Hong, Meng Li, Min Yang, Sadhan Jana, Fabia Gamboni, Emily Tsao, Weiyi Liu, John E. Dick, Hening Lin, Ari Melnick, Anastasia Tikhonova, Andrea Arruda, Mark D. Minden, Brian Raught, Angelo D'Alessandro, Courtney L. Jones
Summary: This study identifies SIRT3 as a critical target for the survival of primary human LSC and demonstrates that it regulates fatty acid oxidation (FAO) to support OXPHOS and ATP production in human LSC. Inhibition of SIRT3 sensitizes LSC to cholesterol esterification and the BCL-2 inhibitor venetoclax.
Article
Chemistry, Organic
Raushan Kumar Jha, Monojit Batabyal, Sangit Kumar
Summary: In this study, a blue-light-driven amination of C-(sp (2))-H bond of naphthoquinones and quinones with the N-H bond of primary and secondary amines was reported, leading to the synthesis of 2-amino-naphthoquinones and 2-amino-quinones. The reaction was selectively achieved in methanol solvent without using any additional reagents, additives, and oxidant under blue light irradiation. The reaction mechanism involves a radical pathway. Overall, this study provides a convenient and efficient method for the synthesis of valuable compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Michael R. Smith, Le Zhang, Yizhen Jin, Min Yang, Anusha Bade, Kevin D. Gillis, Sadhan Jana, Ramesh Naidu Bypaneni, Timothy E. Glass, Hening Lin
Summary: Maintaining the balance of amino acids is important for cell survival and dysfunction of nutrient balance can lead to diseases such as diabetes. In this study, a novel fluorescent sensor called NS560 was developed to detect 18 proteogenic amino acids in mammalian cells. By using NS560, amino acid pools were identified in lysosomes, late endosomes, and near the rough endoplasmic reticulum. Furthermore, the study revealed that Cathepsin L (CTSL) is the target of chloroquine, leading to the accumulation of amino acids in large cellular foci.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Monojit Batabyal, Saket Jain, Aditya Upadhyay, Saravanan Raju, Sangit Kumar
Summary: A one pot Cu(I)-assisted synthetic methodology has been developed to prepare biologically important C-2-symmetric spirodiaza, benzyloxy and benzoxytelluranes. These compounds can serve as potent catalysts for the reduction of H2O2 and nitro-Michael reactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Aditya Upadhyay, Harshita Meena, Raushan Kumar Jha, Kanika, Sangit Kumar
Summary: A series of novel copper(ii) phenolate selenoether complexes were synthesized and characterized. The complexes showed Jahn-Teller distortion, with the distorted square pyramidal geometry being optimal for electrocatalyzing the hydrogen evolution reaction with high efficiency.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
