Article
Chemistry, Physical
Carmen Mejuto, Laura Ibanez-Ibanez, Gregorio Guisado-Barrios, Jose A. Mata
Summary: This study describes an effective visible-light-promoted iridium catalyst that enables hydrogen production at room temperature without additives. The single iridium complex in the photocatalytic system plays a dual role in harvesting visible light and facilitating C-H cleavage and H-2 formation. The presence of specific ligands in the iridium complex is crucial for the photocatalytic transformation, and the complex also acts as an efficient catalyst for thermal reverse process under mild conditions.
Article
Chemistry, Multidisciplinary
Pep Rojo, Medea Molinari, Albert Cabre, Clara Garcia-Mateos, Antoni Riera, Xavier Verdaguer
Summary: Chiral compounds containing nitrogen heteroatoms are crucial for the chemical, pharmaceutical, and agrochemical industries. In this study, a series of P-stereogenic phosphinooxazoline iridium catalysts were synthesized and successfully used in the asymmetric hydrogenation of N-Boc-2,3-diarylallyl amines, achieving high enantioselectivity. The synthetic utility of the obtained 2,3-diarylpropyl amines was also demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Maria Biosca, Pol de la Cruz-Sanchez, Jorge Faiges, Jessica Margalef, Ernest Salomo, Antoni Riera, Xavier Verdaguer, Joan Ferre, Feliu Maseras, Maria Besora, Oscar Pamies, Montserrat Dieguez
Summary: Ir-MaxPHOX-type catalysts exhibit high catalytic performance in the hydrogenation of a wide range of nonchelating olefins with different geometries, substitution patterns, and degrees of functionalization. These air-stable and readily available catalysts have been successfully used in the asymmetric hydrogenation of di-, tri-, and tetrasubstituted olefins (ee ' s up to 9996). The combination of theoretical calculations and deuterium labeling experiments has revealed the factors responsible for the observed enantioselectivity, allowing for the rationalization of suitable substrates for these Ircatalysts.
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Xianjun Xu, Huangdi Feng, Erik V. Van der Eycken
Summary: An efficient palladium-catalyzed reaction under microwave irradiation has been developed for the construction of 4-substituted isoquinolines through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade. The practical value of this method was demonstrated by conducting millimole-scale reactions and transforming the isoquinoline into a key intermediate for the synthesis of a lamellarin analogue.
Article
Chemistry, Organic
Pep Rojo, Agusti Lledos, Antoni Riera, Xavier Verdaguer
Summary: A threonine-derived phosphine-oxazoline iridium catalyst with excellent selectivity in the hydrogenation of N-Boc-2,3-diarylallylamines is reported. The reversible cyclometallation process and the influence of substitution at the phenyl group of the oxazoline on this equilibrium are thoroughly investigated. X-Ray analysis reveals the coordination mode of the cyclometallated tridentate ligand. Furthermore, the utilization of Ir(III) pre-catalysts or Ir(I)/Ir(III) mixtures in hydrogenation reactions is proposed based on the observed equilibrium dynamics.
Article
Chemistry, Applied
Maria Biosca, Pol de la Cruz-Sanchez, Daniel Tarr, Patricia Llanes, Erik A. Karlsson, Jessica Margalef, Oscar Pamies, Miquel A. Pericas, Montserrat Dieguez
Summary: A chiral phosphine-triazole ligand has been developed for the Ir-catalyzed asymmetric hydrogenation of exocyclic benzofused alkenes, which overcomes previous limitations and exhibits excellent enantioselectivity. The catalyst shows good tolerance towards various substituents and substitution patterns at both aromatic rings, making it an effective tool for hydrogenation of exocyclic olefins.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Inorganic & Nuclear
Santanu Malakar, Benjamin M. Gordon, Souvik Mandal, Thomas J. Emge, Alan S. Goldman
Summary: The reaction between [(p-cymene)RuCl2]2 and the triphosphine ligand bis(2-di-tert-butylphosphinophenyl)phosphine (tBuPHPP) leads to an exchange reaction where a chloride ligand and a phosphorus-bound H atom are exchanged to form the (chlorophosphine)ruthenium hydride complex (tBuPClPP)RuHCl. The thermodynamics of Cl-P/Ru-H exchange depends on the nature of the ancillary ligand. This study has implications for five-coordinate d6 complexes.
INORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Rizk E. Khidre, Ibrahim M. A. Radini, Tahah A. Ameen, Ahmed A. M. Abdelgawad
Summary: This review discusses the synthetic methods and pharmacological properties of [1,2,3]triazoloquinoline derivatives, including the ten isomers based on the junction between triazole and quinoline. The synthetic methods are categorized into groups based on the type of isomers, and the pharmacological activity of [1,2,3]triazoloquinoline is also addressed in the review.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Yin-Feng Ma, Chuan-Jin Hou, De-Quan Wei, Xinwei He, Ting-Ting Chu, Xiu-shuai Chen, Xiang-Ping Hu
Summary: The asymmetric hydrogenation of beta-ketophosphonates with chiral Ir/P,N,N-ligands catalyst leads to high yields of beta-hydroxyphosphonates with good or excellent enantioselectivities under mild conditions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Biswajit Panda, Gianluigi Albano
Summary: Nicotine, a chiral alkaloid found in tobacco plants, targets and stimulates nicotinic acetylcholine receptors, leading to interest in developing synthetic analogues. Current research focuses on synthesizing conformationally restricted analogues of nicotine using various catalytic processes. Biological studies on the activity of these analogues on specific nAChR subunits are also considered.
Review
Chemistry, Organic
Rizk E. Khidre, Mohamed S. Mostafa, Yousef E. Mukhrish, Mounir A. Salem, Mohamed S. Behalo
Summary: This review examines the synthetic methods of pyrazolo[1,2-b]phthalazine derivatives using one-pot multi-component reactions, categorizing them according to the reactant types. Various methods were reported.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bram B. C. Peters, Norman Birke, Luca Massaro, Pher G. Andersson
Summary: The catalytic asymmetric hydrogenation of olefins is a powerful method for synthesizing chiral compounds. By using an iridium N,P-complex catalyst, various prochiral unsaturated amides can be efficiently reduced with high enantioselectivities. The attractive features of this method include its application in the synthesis of fenpropidin and the potential use of isomeric mixtures as starting materials.
Article
Chemistry, Multidisciplinary
Gaspard Hedouin, Sudripet Sharma, Karanjeet Kaur, Ramesh Hiralal Choudhary, Jacek B. Jasinski, Fabrice Gallou, Sachin Handa
Summary: In this study, recyclable ligand-free iridium (Ir)-hydride based Ir-0 nanoparticles (NPs) were developed for the selective partial hydrogenation of P-V-substituted naphthalenes. Both isolated and in situ generated NPs showed catalytic activity. Metal-surface-bound hydrides were observed in the NMR study, likely formed from Ir-0 species. Hexafluoroisopropanol as a solvent was found to activate the substrate through hydrogen bonding. The highly regioselective aromatic ring reduction was demonstrated in different phosphine oxides or phosphonates using the NPs as catalysts. The study also presented a novel approach for preparing H-8-BINAP and its derivatives without losing enantioselectivity during catalytic events.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Florian Bourriquen, Julien Hervochon, Stephan Bartling, Nils Rockstroh, Ceidric Fischmeister, Kathrin Junge, Matthias Beller
Summary: A methodology for regiodivergent hydrogenation of quinolines is presented using readily available and commercial supported ruthenium catalysts. cis- or trans-Decahydroquinolines can be obtained with high yield and high diastereoselectivity by adjusting the catalyst or reaction temperature. Heterogeneous ruthenium catalysts are reported for practical regiodivergent hydrogenation of quinolines.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Applied
Liu-Yang Pu, Ji-Qiang Chen, Mao-Lin Li, Yao Li, Jian-Hua Xie, Qi-Lin Zhou
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Organic
Liu-Yang Pu, Fan Yang, Ji-Qiang Chen, Ying Xiong, Huai-Yu Bin, Jian-Hua Xie, Qi-Lin Zhou
Article
Chemistry, Applied
Liu-Yang Pu, Fan Yang, Ji-Qiang Chen, Ying Xiong, Jian-Hua Xie, Qi-Lin Zhou
Summary: The enantioselective total synthesis of the pentacyclic proaporphine alkaloid (-)-misramine was achieved, featuring key reactions including Pictet-Spengler cyclization and Baeyer-Villiger oxidation. The absolute configuration of the pentacyclic framework was determined through X-ray single-crystal analyses.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Liu-Yang Pu, Zhiyue Li, Feijuan Huang, Limin Li, Yucui Ma, Min Ma, Shengquan Hu, Zhengzhi Wu
Summary: This study synthesized a series of novel colchicine-magnolol hybrids and found that they exhibited inhibitory effects on both the coronavirus 3CL(pro) and neutrophil elastase, which colchicine and magnolol alone did not possess.
NATURAL PRODUCT RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Zhiyue Li, Shengquan Hu, Liu-Yang Pu, Ziwen Li, Guanbao Zhu, Yongkai Cao, Limin Li, Yucui Ma, Zhanyan Liu, Xinping Li, Guangjie Liu, Keji Chen, Zhengzhi Wu
Summary: In this study, a novel hybrid CMH was designed and synthesized, which showed stronger anti-cancer activity against lung carcinoma cells compared to colchicine, with lower toxicity on normal lung cells. In a mouse model, CMH effectively inhibited tumor growth and showed higher efficacy than cisplatin. Mechanistic studies revealed that CMH suppressed the protein expression of phosphorylated ERK and molecular docking analysis indicated its binding to the colchicine binding site of tubulin. These findings suggest that CMH has potential as an antineoplastic agent and provide a basis for further investigation and confirmation of its therapeutic potential.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Liu-Yang Pu, Zhiyue Li, Limin Li, Yucui Ma, Shengquan Hu, Zhengzhi Wu
Summary: In this study, we describe a concise and enantioselective total synthesis of isopavine alkaloids with a unique azabicyclo[3.2.2]nonane tetracyclic skeleton. Key steps include iridium-catalyzed asymmetric hydrogenation, Curtius rearrangement, and Eschweiler-Clarke methylation, enabling the synthesis of isopavine alkaloids in 6-7 linear steps. Additionally, we discovered that isopavine alkaloids, particularly (-)-reframidine (3), exhibit significant antiproliferative effects on various cancer cell lines for the first time.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yan Li, Liu-Yang Pu, Yayun Li, Guanbao Zhu, Zhengzhi Wu
Summary: In this study, a hybrid compound consisting of myricetin and nobiletin was synthesized and evaluated for its biological activity. The results showed that the compound, named MNH, effectively reduced serum uric acid levels and repaired renal histopathological damage. Furthermore, MNH modulated gut microbiota and metabolic pathways, indicating its potential protective effect against hyperuricemia.
Article
Chemistry, Organic
Bohua Long, Liuyang Pu, Zhanyan Liu, Xiaobin Zeng, Zhengzhi Wu
Summary: A convergent procedure has been developed for the formal synthesis of cyclotheonellazole A, achieving high yields and excellent stereoselectivity. Notably, the synthesis involves efficient preparation of O-pivaloyl-protected alpha-hydroxy-beta-amino amides and a one-pot process for introducing the challenging thiazole moiety. The overall synthetic approach is highly efficient and holds promise for the generation of analogues in drug development.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Pu Liu-Yang, Li Zhiyue, Li Limin, Ma Yucui, Ma Min, Hu Shengquan, Wu Zhengzhi
Summary: (-)-Colchicine and (-)-N-acetylcolchinol methyl ether were synthesized using a concise asymmetric synthetic approach. The carbon framework was constructed through Aldol condensation of simple aldehydes and ketones, followed by the economical and efficient synthesis of chiral amine intermediates through asymmetric reductive amination with chiral tert-butanesulfinamide. The 3-rings skeleton of colchicine and related alkaloids was then constructed by oxidation with hypervalent iodine reagent. This strategy provides an efficient method for the convenient and economical synthesis of these alkaloids.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
