Article
Chemistry, Multidisciplinary
Ren-Xiao Liang, Jian-Fei Chen, Ying-Ying Huang, Ya-Ping Yu, Han-Yue Zhang, Yu-Feng Song, Gavin Chit Tsui, Yi-Xia Jia
Summary: Highly enantioselective palladium-catalyzed dearomative reductive Heck reaction and domino Heck-Suzuki reaction of 2-CF3-indoles have been developed. A variety of indolines bearing different stereocenters can be obtained using different reaction systems.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Mei-Ling Wang, Hui Xu, Han-Yuan Li, Biao Ma, Zhen-Yu Wang, Xing Wang, Hui-Xiong Dai
Summary: The Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is achieved via palladium-catalyzed ligand-promoted C-C bond cleavage, providing good to excellent yields of the alkene product. Further applications in the late-stage olefination of drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By using ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved through sequential ortho-C-H alkylation/ipso-Heck olefination.
Article
Chemistry, Organic
Min Xiang, Chen-Yi Li, Jian Zhang, Ying Zou, Zhi-Cheng Huang, Wen-Sheng Li, Yi Wang, Fang Tian, Li-Xin Wang
Summary: The study demonstrates an organocatalyst promoted diastereoselective and enantioselective reaction, allowing for the efficient and mild synthesis of a broad range of new and versatile dihydrobenzofurans containing chiral hemiketal and succinimide frameworks. The reaction yields moderate to excellent results (up to 95%) with good to excellent enantioselectivities (up to 95 : 5 er) and diastereoselectivities (all with at least 99 : 1 dr).
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ajaz Ahmed, Norein Sakander, Faheem Rasool, Nazar Hussain, Debaraj Mukherjee
Summary: 1,2-Annulated pyranose sugars fused with six membered rings have emerged as an important class of carbohydrates. In this study, we describe a zinc chloride catalyzed one pot diastereoselective synthesis of sugar fused dioxazinanes, which can proceed smoothly under mild reaction conditions using various aromatic nitrones with different substituents.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Na Luo, Zhen-Wei Sun, Xing-Xin Xu, Xiao-Qiang Hu, Feng-Cheng Jia
Summary: A one-step, transition-metal-free, base-promoted cascade reaction of 2-halogenated arylglyoxals with 2-oxindoles provides a straightforward approach to structurally diverse N-protection free indole-indenones in satisfactory yields. Control experiments indicated the crucial role of the geminal bisindolin-2-one intermediate in the downstream annulation/ring-cleavage/ring-reconstruction reaction sequence. This novel reaction not only enriches the reactivity of indolin-2-ones as the recursive enolate anion source, but also achieves thermal-induced alpha-arylation of oxindoles without a transition-metal catalyst.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Anushka Koranne, Shrishty Turakhia, Vikesh Kumar Jha, Sangeeta Gupta, Rangnath Ravi, Abhijeet Mishra, Anil K. Aggarwal, Chandan Kumar Jha, Neelu Dheer, Abadh Kishor Jha
Summary: This review discusses the palladium-catalyzed Mizoroki-Heck cross-coupling reactions, which involve the formation of substituted olefins through a typical Heck coupling mechanism, unlike the direct cross-coupling of alkenes with aryl halides in Heck olefination. These reactions address the issue of alkene polymerization at high temperatures and enhance reaction efficiency by reducing reaction time and purification steps.
Article
Chemistry, Multidisciplinary
Jakub Vaith, Dasha Rodina, Gregory C. Spaulding, Shauna M. Paradine
Summary: We developed ureas as sterically undemanding pro-ligands for Pd catalysis. N-Arylureas showed better performance than phosphine ligands in Pd-catalyzed reactions, enabling the heteroannulation of N-tosyl-o-bromoanilines and 1,3-dienes to prepare 2-substituted indolines, even with sterically demanding substrates. Experimental and computational studies confirmed the monodentate binding through the nonsubstituted nitrogen in Pd-urea complexes, which is uncommon for metal-ureate complexes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Vitor A. Fernandes, Rafaely N. Lima, Yoisel B. Broterson, Meire Y. Kawamura, Radell Echemendia, Alexander F. de la Torre, Marco A. B. Ferreira, Daniel G. Rivera, Marcio W. Paixao
Summary: An efficient strategy combining stereocontrol of organocatalysis with diversity-generating character of multicomponent reactions was used to produce structurally unique, tetrasubstituted cyclopentenyl frameworks. This approach yielded a diversity of structurally complex compounds with high stereoselectivity and moderate to high yields, including peptidomimetics and natural product hybrids.
Article
Chemistry, Multidisciplinary
Mengting Zeng, Ying Xue, Yunan Qin, Fen Peng, Quan Li, Ming-Hua Zeng
Summary: This study investigated the low-cost CuBr-promoted domino Biginelli reaction under solvothermal conditions and successfully synthesized novel bridged polyheterocycles. The reaction mechanism was elucidated, and the antitumor activity of the synthesized compounds was evaluated. The findings suggest that the synthesized polyheterocycles have potential medicinal value and provide fragmentation rules for rapid structural identification.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Ming Chen, Xing-Xing Xu, Xucai Wang, Zhi-Hui Ren, Zheng-Hui Guan
Summary: A highly enantioselective palladium-catalyzed Heck/Suzuki cascade reaction of N-(2-bromophenyl)acrylamides has been developed. The key to the success of this transformation was found to be the endo-5-norbornene-2,3-dimethanol helping prevent transmetalation of the aryl-palladium complex. The reaction was shown to tolerate a wide range of functional groups and provide straightforward access to an array of oxindoles with excellent ee values.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Organic
Shan Shan Ng, Wai Hang Pang, On Ying Yuen, Chau Ming So
Summary: This article provides an overview of the development of palladium-catalyzed coupling reactions and the effects of ligand properties on the chemoselectivity of aryl (pseudo)halides. The selectivity of coupling reactions can be significantly influenced by applying appropriate ligands. This review discusses the chemoselectivity of various catalysts and presents successful examples of sequential chemoselective coupling approaches, demonstrating the capacity of catalysts to regulate chemoselectivity and their implications for synthesizing valuable compounds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Kunpeng Wang, Jingping Li, Haoxiang Zhang, Yan Chen, Mengfan Li, Junju Xu, Benren Liao, Weiyin Yi
Summary: Researchers have developed a novel method for synthesizing symmetrical and unsymmetrical fuchsones using p-QMs or substituted phenols as aryl sources under metal-free conditions with the promotion of DMSO. These unprecedented strategies have significant advantages and are important for further exploration of fuchsones and the development of new applications.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Tetsuya Tsujihara, Takeyuki Suzuki, Tomikazu Kawano
Summary: A convenient and catalytic method for the diastereoselective construction of cis-1,3-disubstituted isoindoline skeletons has been developed, achieving complete diastereocontrol in the synthesis of a series of cis-1,3-disubstituted isoindoline-aminal hybrid compounds through direct aminalization of N-protected imines with a Michael acceptor and subsequent intramolecular aza-Michael reaction.
Article
Polymer Science
Daniele Conelli, Nicola Margiotta, Roberto Grisorio, Gian Paolo Suranna
Summary: In recent years, the importance of C-H bond activation in the synthesis of conjugated polymers has been emphasized. By using environmentally friendly solvents, efficient synthesis of high molecular weight and regioregular conjugated polymers can be achieved.
MACROMOLECULAR CHEMISTRY AND PHYSICS
(2021)
Review
Chemistry, Applied
Christopher S. Horbaczewskyj, Ian J. S. Fairlamb
Summary: This review analyzes the use of ppm level palladium concentrations in catalytic cross-coupling reactions and their relationship to mole percentage. It suggests that ppm level palladium could be a practical descriptor of catalyst quantities in palladium-catalyzed cross-coupling reactions. The study also compares palladium with other metal catalyst systems, providing insights into the spread of ppm palladium across various studies in cross-coupling chemistry literature.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Biochemical Research Methods
Sheenu Abbat, Chaitanya K. Jaladanki, Prasad V. Bharatam
JOURNAL OF MOLECULAR GRAPHICS & MODELLING
(2019)
Article
Chemistry, Organic
Monika Bhardwaj, Faheem Rasool, Madhu Babu Tatina, Debaraj Mukherjee
Article
Chemistry, Organic
Madhu Babu Tatina, Xia Mengxin, Rao Peilin, Zaher M. A. Judeh
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Microbiology
Ziying Han, Shantoshini Dash, Cari A. Sagum, Gordon Ruthel, Chaitanya K. Jaladanki, Corbett T. Berry, Michael P. Schwoerer, Nina M. Harty, Bruce D. Freedman, Mark T. Bedford, Hao Fan, Sachdev S. Sidhu, Marius Sudol, Olena Shtanko, Ronald N. Harty
Review
Pharmacology & Pharmacy
Chaitanya K. Jaladanki, Anuj Gahlawat, Gajanan Rathod, Hardeep Sandhu, Kousar Jahan, Prasad V. Bharatam
DRUG METABOLISM REVIEWS
(2020)
Article
Chemistry, Organic
Madhu Babu Tatina, Wang Xinzhu, Mardi Santoso, Ziad Moussa, Zaher M. A. Judeh
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Toxicology
Chaitanya K. Jaladanki, Yang He, Li Na Zhao, Sebastian Maurer-Stroh, Lit-Hsin Loo, Haiwei Song, Hao Fan
Summary: The study proposed a virtual screening method based on molecular docking to predict potential endocrine-disrupting chemicals that bind to nuclear receptors. By analyzing the discriminating power of multiple structures for NRs and optimizing the strategy with a chemical similarity-weighted scoring scheme, several fatty acids were screened as potential EDCs.
ARCHIVES OF TOXICOLOGY
(2021)
Article
Biology
Birgit Eisenhaber, Swati Sinha, Chaitanya K. Jadalanki, Vladimir A. Shitov, Qiao Wen Tan, Fernanda L. Sirota, Frank Eisenhaber
Summary: Through careful sequence analysis and structural modeling, it can be concluded that TMTCs are enzymatically active sugar transferases belonging to the GT-C/PMT superfamily. The DUF1736 segment, the loop between TM7 and TM8, is critical for catalysis and lipid-linked sugar moiety binding.
Article
Chemistry, Organic
Mengxin Xia, Mallikharjuna Rao Lambu, Madhu Babu Tatina, Zaher M. A. Judeh
Summary: This study developed a practical and efficient three-component reaction to synthesize densely functionalized pyrroles from common carbohydrates. The cascade reaction showed high selectivity and catalytic efficiency, suitable for large-scale synthesis and further transformation to more complex structures. The work represents a significant advancement in sustainable synthesis of these ubiquitous heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Virology
Jingjing Liang, Gordon Ruthel, Cari A. Sagum, Mark T. Bedford, Sachdev S. Sidhu, Marius Sudol, Chaitanya K. Jaladanki, Hao Fan, Bruce D. Freedman, Ronald N. Harty
Summary: The study identified the host WW-domain-containing protein WWOX as a novel interactor with VP40 and Z proteins, demonstrating that WWOX inhibits budding of VP40/Z VLPs and live virus in a PPxY/WW-domain-dependent manner. These findings expand the repertoire of host interactors regulating PPxY-mediated budding of RNA viruses and highlight competitive interplay and modular virus-host interactions impacting both the virus life cycle and the host cell.
JOURNAL OF VIROLOGY
(2021)
Article
Virology
Ariel Shepley-McTaggart, Michael Patrick Schwoerer, Cari A. Sagum, Mark T. Bedford, Chaitanya K. Jaladanki, Hao Fan, Joel Cassel, Ronald N. Harty
Summary: The study identified E3 ubiquitin ligase SMURF2 as a novel interactor with VP40 that positively regulates the release of VP40 VLP. Understanding the modular interplay between filovirus VP40 and host proteins may lead to the development of new therapies to combat deadly infections.
Article
Chemistry, Organic
Madhu Babu Tatina, Mohammad Saif Ali, P. Ramesh, Subhash Ghosh
Summary: We present a strategy for the stereoselective synthesis of 1,2-trans-glycosides in the absence of neighboring group participation. The protocol relies on catalyst control instead of protecting group selection, and has been successfully applied for the preparation of various glycosides.
Article
Chemistry, Multidisciplinary
P. Ramesh, Mohamad Saif Ali, Subhash Ghosh, Madhu Babu Tatina
Summary: A simple and environmentally friendly method for the synthesis of glycosides using citric acid mediation has been reported. Under mild reaction conditions, a wide range of glycosides, with the α-isomer as the major product, were prepared from D-glucal, L-rhamnal, D-xylal, and D-galactal with various alcohols, yielding up to 80%.
RESULTS IN CHEMISTRY
(2022)
Meeting Abstract
Pharmacology & Pharmacy
S. Khatun, C. Jaladanki, P. V. Bharatam
NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Madhu Babu Tatina, Ziad Moussa, Mengxin Xia, Zaher M. A. Judeh
CHEMICAL COMMUNICATIONS
(2019)
