Article
Chemistry, Physical
Renat Kadyrov
Summary: An efficient and simple catalytic system has been developed for the hydrogenation of carboxylic esters using commercially available Ru-salts and imidazolium salts. This combination enables the reduction of esters to alcohols at moderate temperature and pressure, offering a practical method for alcohol synthesis.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Xintuo Yang, Xiang Li, Pinhong Chen, Guosheng Liu
Summary: A novel Pd(II)-catalyzed enantioselective Markovnikov hydrooxygenation of unactivated terminal alkenes using a substituted pyridinyl oxazoline (Pyox) ligand has been developed. The (EtO)(2)MeSiH/BQ redox system is crucial for the highly selective and efficient hydrooxygenation, where alkylpalladium(II) species generated from enantioselective oxypalladation step is reduced by silane. This method provides an efficient access to optically pure alcohol esters from easily available alkenes with excellent enantioselectivities and features a broad substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Niklas F. Both, Anke Spannenberg, Haijun Jiao, Kathrin Junge, Matthias Beller
Summary: The use of bis(NHC) manganese(I) complexes 3 as catalysts for the hydrogenation of esters was investigated. Various aromatic and aliphatic esters were successfully hydrogenated at mild temperatures and low catalyst loadings using complexes 3 with KHBEt3 as additive, highlighting the efficiency of the novel catalytic system. Additionally, the versatility of the developed catalytic system was demonstrated by the hydrogenation of other substrate classes like ketones, nitriles, N-heteroarenes, and alkenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chenghao Li, Shu-Xin Zhang, Yu Feng, Yan-Mei He, Qing-Hua Fan
Summary: The chiral ruthenium-catalyzed enantioselective hydrogenation of tetrapyridine-type N-heteroarenes was developed for the first time. The adjacent tetraheteroaromatic substrates showed high reactivity, enantioselectivity, and diastereoselectivity, with yields up to 93%, enantiomeric excess (>99% ee), and diastereomeric ratio of 92:8, respectively, in the presence of phosphine-free chiral cationic ruthenium diamine complexes. The potential application of chiral tetradentate pyridine-amine products as chiral ligands was demonstrated in the Cu-catalyzed asymmetric Friedel-Crafts alkylation reaction between indoles and nitroalkenes.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shu-Xin Zhang, Cong Xu, Niannian Yi, Shan Li, Yan-Mei He, Yu Feng, Qing-Hua Fan
Summary: This study successfully achieved the highly efficient ruthenium-catalyzed enantioselective hydrogenation of 9-phenanthrols by trapping the unstable keto tautomers under mild conditions. The method provides a facile access to chiral 9,10-dihydrophenanthren-9-ols with high yield and enantiomeric excess.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Daniel J. Tindall, Steffen Mader, Alois Kindler, Frank Rominger, A. Stephen K. Hashmi, Thomas Schaub
Summary: Sugar alcohols are important for the food industry and can be produced in large quantities with increased yield and stereoselectivity through a homogeneous system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jana Hatzfeld, Steffen Skowaisa, Elisabeth Jackel, Julia Kaufmann, Edgar Haak
Summary: Various triaminocyclopentadienyl ruthenium complexes were synthesized from Ru-3(CO)(12) and tested for their ability to catalyze cascade conversions of propargyl alcohols. The substrate scope of catalytic cycloadditions was extended to terpenoid-derived propargyl alcohols containing an internal alkyne moiety, resulting in a wide range of cyclic terpenoid and phloroglucinol adducts obtained by complementary application of both types of catalysts.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Zhikun Zhang, Xile Hu
Summary: A catalytic deracemization method for secondary benzylic alcohols has been developed, utilizing sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation. The combination of a heterogeneous dehydrogenation photocatalyst and a chiral molecular hydrogenation catalyst enables the conversion of racemic aryl alkyl alcohols into their enantiomerically enriched forms.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Steffen Skowaisa, Edgar Haak
Summary: A highly effective catalyst for the alkylation of poorly reactive alcohols with indoles or ketones has been discovered. This catalyst is readily available, stable in air and moisture, and exhibits wide functional group tolerance.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Andrej Emanuel Cotman
Summary: Noyori-Ikariya-type ruthenium(II)-catalysts have been used for 25 years in asymmetric transfer hydrogenation for the synthesis of chiral secondary alcohols. Recent progress has been made in understanding the asymmetric reduction of complex ketones, controlling up to four stereocenters in a single transformation. Intriguing multi-chiral molecular architectures can be prepared via ATH for drug discovery.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Tanuja Tewari, Rohit Kumar, Amol C. Chandanshive, Samir H. Chikkali
Summary: Metal-catalyzed hydroformylation and hydrogenation heavily rely on ligands, with phosphorus ligands playing a pivotal role. This account presents three distinct classes of phosphorus ligands, their synthesis, performance in reactions, and the latest developments in iron-catalyzed hydroformylation of alkenes. The use of phosphines enabled iron-catalyzed hydroformylation under mild conditions, demonstrating the central role of phosphorus ligands in industrially relevant transformations.
Article
Chemistry, Organic
Gollapalli Narasimha Rao, Govindasamy Sekar
Summary: An efficient and reusable catalyst composed of copper-oxide nanoparticles and (R)-(-)-DTBM SEGPHOS has been developed for the chemo- and enantioselective reduction of alpha-keto amides to alpha-hydroxy amides. The reaction showed excellent enantioselectivity and good yields for various alpha-keto amides containing different electron-donating and electron-withdrawing groups. The copper-oxide nanoparticle catalyst maintained its size, reactivity, and enantioselectivity after being reused for four catalytic cycles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Francisco Gaspar, Guilherme S. Caleffi, Paulo C. T. Costa-Junior, Paulo R. R. Costa
Summary: The Noyori-Ikariya Ru-II complexes were utilized to promote the reduction of C=C/C=O bonds in isoflavones, leading to selective formation of cis-3-phenylchroman-4-ols with different substituents at the 2' position of the B-ring in high yields and excellent enantioselectivities. New synthetic strategies for obtaining enantioenriched isoflavanones and pterocarpans were also demonstrated in this study, showcasing the versatility of the developed method.
Article
Chemistry, Physical
Masa Sterle, Matej Hus, Matic Lozinsek, Anamarija Zega, Andrej Emanuel Cotman
Summary: Stereopure CF3-substituted syn-1,2-diols were synthesized through the reductive dynamic kinetic resolution of corresponding alkyl ketones, yielding products with >95% ee and >87:13 syn/anti ratio. This method provides a rapid access to stereopure bioactive molecules. Moreover, DFT calculations were conducted on three types of Noyori-Ikariya ruthenium catalysts to demonstrate their general ability to control stereoselectivity through hydrogen bond acceptor SO2 region and CH/pi interactions.
Article
Chemistry, Physical
Jingjing Zhang, Heng-Ding Wang, Yifei Zhang, Zhiwen Li, Dongyuan Yang, Dong H. Zhang, Tatsuya Tsukuda, Gao Li
Summary: Au25(PPh3)10(SC2H4Ph)5Cl2]2+ (Au25) supported on TiO2 (P25) exhibits distinct photocatalytic behaviors in the oxidation of amines using visible or ultraviolet light. The activity under visible light (455 nm) was superior to that under ultraviolet light. Through investigation of the photoreaction pathways of Au25 upon irradiation with different wavelengths, it was found that the inferior photocatalytic activity of Au25/P25 under ultraviolet light is mainly due to the poor photostability of Au25.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Francesco Santoro, Martin Althaus, Cristina Bonaccorsi, Sebastian Gischig, Antonio Mezzetti
Article
Chemistry, Inorganic & Nuclear
Martin Althaus, Cristina Bonaccorsi, Antonio Mezzetti, Francesco Santoro
Article
Chemistry, Inorganic & Nuclear
C Bonaccorsi, F Santoro, S Gischig, A Mezzetti
Article
Chemistry, Inorganic & Nuclear
F Maienza, F Santoro, F Spindler, C Malan, A Mezzetti
TETRAHEDRON-ASYMMETRY
(2002)
