Article
Chemistry, Organic
Lalita Tanwar, Jonas Boergel, Johannes Lehmann, Tobias Ritter
Summary: Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. The strategy presented here allows for selective C-H iodination of (hetero)arenes with a broad functional group tolerance, showcasing the utility and differentiation from other iodination methods for a set of carboarenes and heteroarenes.
Review
Chemistry, Physical
Damian E. Yerien, Beatriz Lantano, Sebastian Barata-Vallejo, Al Postigo
Summary: This article introduces fluoroalkylation strategies for alkoxy-substituted (hetero)arenes using photocatalytic and thermal methods, involving various photocatalysts and fluoroalkylating reagents, as well as electrocatalytic methods for trifluoromethylation reactions using CF3 radicals, and implementation of thermal methodologies with Pd(OAc)(2) catalysis and CF3Br as trifluoromethylating source.
Article
Chemistry, Multidisciplinary
Jay S. Wright, Liam S. Sharninghausen, Sean Preshlock, Allen F. Brooks, Melanie S. Sanford, Peter J. H. Scott
Summary: This article presents a novel method for the meta-selective C-H radiofluorination of (hetero)arene substrates. The process can be conducted on a benchtop without the need for Schlenk or glovebox techniques, resulting in higher yields and purity of the products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Wenjie Jiang, Fangjun Shao, Jiaxu Cheng, Fandong Ma, Zhongzhe Wei, Xing Zhong, Hong Wang, Jianguo Wang
Summary: Deuterium-labeled aromatics are crucial for the production of fine chemicals. A Pt/Ca12Al14Ox catalyst with complex valence was synthesized and successfully used for the deuteration of toluene using inexpensive D2O. It exhibited high deuteration efficiency, achieving 96% deuteration in just 4 hours, surpassing the performance of commonly used Pt/C catalyst. The catalyst can also be reused up to 16 times, showing good stability.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Alexander A. A. Fadeev, Gabriele Manca, Martin Kotora
Summary: A synthesis of 1,4-diborylated benzenes from alkynes and ethynyl boronate was achieved using Ru-catalyzed regioselective co-cyclotrimerization. The reaction showed good applicability to alkynes with metal-coordinating groups, giving useful diborylated benzenes in modest yields. DFT calculations provided insights into the reaction mechanism and the reason for its remarkable regioselectivity. Selected diborylated benzenes were further transformed into various products, including natural bioactive small molecules like quinones and hydroquinones.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Marc Magre, Shengyang Ni, Josep Cornella
Summary: This review evaluates and summarizes the progress in the synthesis of highly fluorinated aryl-S-VI compounds at all levels, discussing synthetic strategies, reactivity, the advantages and disadvantages of the synthetic procedures, the proposed mechanisms, and the potential upcoming opportunities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Gaijun Xue, Fukai Xie, Hongliang Liang, Guoliang Chen, Wen Dai
Summary: In this study, a protocol for the direct synthesis of nitriles via copper-catalyzed oxidative cleavage and cyanation of C-C bonds in various multicarbon alkyl-substituted (hetero)arenes is reported. Mechanistic studies reveal the involvement of a tandem oxidative process in this transformation.
Review
Chemistry, Multidisciplinary
Zhaohong Liu, Paramasivam Sivaguru, Yongquan Ning, Yong Wu, Xihe Bi
Summary: (Hetero)arenes are crucial in pharmaceuticals, materials science, and synthetic chemistry. The controllable modification of these compounds through peripheral and skeletal editing is a challenging goal. This review focuses on the skeletal editing reactions of (hetero)arenes using carbenes, discussing mechanistic considerations and applications in natural product syntheses.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Organic
Liming Cao, Yu Hua, Hong-Gang Cheng, Qianghui Zhou
Summary: Palladium-catalyzed C-H activation has emerged as a versatile strategy for constructing valuable scaffolds, particularly through palladacyclopentane-type intermediates for C-H hetero-functionalization of arenes. Significant progress has been made in this field over the past decade, both in research and applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Stefan Dix, Paul Golz, Jonas R. Schmid, Sebastian Riedel, Matthew N. Hopkinson
Summary: The introduction of bis(trifluoromethyl)peroxide as a practical trifluoromethoxylating reagent opens up a new and efficient method for preparing trifluoromethoxylated arenes. This reagent, easily accessible from inexpensive bulk chemicals, allows for the preparation of trifluoromethoxylated arenes in good yields under mild conditions directly from unactivated aromatics using visible light photoredox or TEMPO catalysis. Additionally, TEMPO catalysis enables the one-step synthesis of valuable pyridine derivatives, simplifying the synthetic process.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Linwei Huang, Wei Liu, Liang-Liang Zhao, Zengyu Zhang, Xiaoyu Yan
Summary: This study investigated the t-BuOK-catalyzed H/D exchange reaction of difluoromethylarenes in DMSO-d(6) solution, which showed excellent deuterium incorporation at the difluoromethyl group. Additionally, the impact of a trace amount of D2O in the DMSO-d(6) solution on the deuteration reaction was also examined.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shiv Shankar Gupta, Manisha, Rakesh Kumar, Ankit Kumar Dhiman, Upendra Sharma
Summary: A regioselective para-C-H halogenation method using SEAr type reaction for N-pyrimidyl (hetero)aromatics has been developed, with wide applicability and high yields for bromination, iodination, and challenging chlorination. The pyrimidyl group acts as a reactivity tuner controlling the regioselectivity, and DFT studies support the observed para-selectivity. Late-stage C-H bromination was also demonstrated on drug/natural molecules to showcase the protocol's applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Yuanyuan Shi, Jean Dinh, Robert Pelletier, Brianne Raccor, Naeem Yusuff, Adam Morgan, Scott Harbeson, Vinita Uttamsingh, Rheem Totah
Summary: Strategically replacing hydrogen with deuterium at sites of metabolism in small molecule drugs can alter drug clearance and enhance clinical safety. Incorporating deuterium at specific sites in bupropion may reduce epimerization, slow metabolism, and decrease the formation of toxic metabolites. Experimental results demonstrate that deuterated bupropion analogues exhibit decreased racemization and formation of certain metabolites in vitro. Selective deuterium substitution at metabolic sites in bupropion has the potential to provide a drug with simplified pharmacokinetics, reduced toxicity, and improved tolerability.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Wu Li, Jabor Rabeah, Florian Bourriquen, Dali Yang, Carsten Kreyenschulte, Nils Rockstroh, Henrik Lund, Stephan Bartling, Annette-Enrica Surkus, Kathrin Junge, Angelika Brueckner, Aiwen Lei, Matthias Beller
Summary: Isotope labelling, especially deuteration, is an important tool for drug development, allowing for identification and quantification of metabolites. This study demonstrates a scalable and efficient method for selective deuteration using a nanostructured iron catalyst.
Article
Chemistry, Multidisciplinary
Lin Wang, Yong Xia, Volker Derdau, Armido Studer
Summary: This study presents a metal-free method for the remote deuterium incorporation into aliphatic C-H bonds in various amides, using inexpensive heavy water as the deuterium source. The method demonstrates high site-selectivity and potential utility for deuterium incorporation into natural product derivatives and drugs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Sayani Mukherjee, P. S. Salini, A. Srinivasan, S. Peruncheralathan
CHEMICAL COMMUNICATIONS
(2015)
Article
Polymer Science
Vanga Mukundam, Atul Kumar, Kunchala Dhanunjayarao, Arthi Ravi, S. Peruncheralathan, Krishnan Venkatasubbaiah
Article
Chemistry, Organic
Manojkumar Janni, Sahil Arora, S. Peruncheralathan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Annaram Thirupathi, Manojkumar Janni, Saravanan Peruncheralathan
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Pragyanditi Dash, Manojkumar Janni, S. Peruncheralathan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Organic
Saravanan Peruncheralathan, Sandra Aurich, Henrik Teller, Christoph Schneider
ORGANIC & BIOMOLECULAR CHEMISTRY
(2013)
Article
Chemistry, Organic
Debashruti Bandyopadhyay, Annaram Thirupathi, Nagsen Munjaji Dhage, Nirmala Mohanta, S. Peruncheralathan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Anwesha Bhattacharya, Annaram Thirupathi, Pradeep Natarajan, Saravanan Peruncheralathan
Summary: A new class of unexplored benzo[b]thiolanes is synthesized for the first time through copper-catalyzed intramolecular S-arylation of trisubstituted thioamides, providing good to excellent yields with fully controlled chemoselectivity. Interestingly, iminobenzo[b]thiolanes are found to be very stable under mild acidic conditions. A plausible mechanism is proposed for the chemoselective S-arylation process.
Article
Chemistry, Organic
Arpita Chatterjee, Divya Radhakrishnan, Debashruti Bandyopadhyay, Selvaraj Kanchithalaivan, Saravanan Peruncheralathan
Summary: Various 2-aryl-3-arylazoacrylonitriles were synthesized by attempting the intramolecular N-arylation of 5-aminopyrazoles using a hypervalent iodine reagent. The synthesis involved the room temperature ring opening of 5-aminopyrazoles assisted by phenyl iodine diacetate. A possible mechanism for the formation of azoalkenes was proposed.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Subhayan Chakraborty, S. Peruncheralathan, Arindam Ghosh
Summary: Paracetamol and other acetanilide derivatives are reported as a special class of diamagnetic Chemical Exchange Saturation Transfer (diaCEST) MRI contrast agents, showing contrast only when molecules form inter-molecular hydrogen bonding. The contrast drops quickly when the hydrogen bond network breaks and high exchange returns. Paracetamol demonstrates 12% contrast at physiological conditions and shows promise as a diaCEST agent for in vivo studies.
Article
Chemistry, Multidisciplinary
M. Murugavel, B. Adinarayana, Mainak Das, S. Peruncheralathan, Narasinga Rao Palepu, A. Srinivasan
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Arpita Chatterjee, Chudamani Murmu, S. Peruncheralathan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Organic
Arindam Ghosh, Syamasrit Dash, A. Srinivasan, C. H. Suresh, S. Peruncheralathan, Tavarekere K. Chandrashekar
ORGANIC CHEMISTRY FRONTIERS
(2019)
Article
Chemistry, Multidisciplinary
Manojkumar Janni, Annaram Thirupathi, Sahil Arora, S. Peruncheralathan
CHEMICAL COMMUNICATIONS
(2017)
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)
