Article
Chemistry, Organic
Xin Cui, Wei Huang, Lipeng Wu
Summary: By using a zirconium-hydride complex as the catalyst, the transfer hydrogenation of quinoline and indole derivatives was achieved with high yields up to 94% and tolerance towards various functional groups. Preliminary mechanistic studies revealed a concerted N-H and B-H activation reaction pathway.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Organic
Congcong Yin, Yingmin Pan, Longsheng Zheng, Bijin Lin, Jialin Wen, Xumu Zhang
Summary: Enantioselective hydrogenation of imines via an outer-sphere mechanism was achieved using an iridium tridentate catalyst, resulting in high enantioselectivities and turnover numbers up to 10,000. This method was successfully applied in the synthesis of chiral amines with an alpha-stereocenter, allowing for the preparation of cinacalcet with remarkably high enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Chenguang Liu, Mingyang Wang, Shihan Liu, Yujie Wang, Yong Peng, Yu Lan, Qiang Liu
Summary: The article reports on the non-noble metal-catalyzed asymmetric hydrogenation of N-heteroaromatics, quinolines. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the reaction, producing high yields and enantioselectivities. The precise regulation of enantioselectivity was ensured by a pi-pi interaction, achieving competitive turnover numbers with noble metal catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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, Organic
Chao Shan, Jinping Xu, Liming Cao, Chaoming Liang, Ruihua Cheng, Xiantong Yao, Maolin Sun, Jinxing Ye
Summary: This study developed a practical continuous flow protocol for efficient synthesis of various functionalized piperidines within minutes, with high yields and enantiomeric excess. The scalability and utility of the process were demonstrated through the efficient synthesis of a drug precursor.
Article
Chemistry, Multidisciplinary
Haibo Wu, Hao Su, Erik J. Schulze, Bram B. C. Peters, Mark D. Nolan, Jianping Yang, Thishana Singh, Marten S. G. Ahlquist, Pher G. Andersson
Summary: The study presents a highly efficient desymmetrization of 1,4-dienes through iridium-catalyzed site- and enantioselective hydrogenation, allowing the installation of two adjacent stereogenic centers. High yields and excellent selectivities were achieved for a range of substrates, and the methodology was demonstrated by synthesizing key intermediates of natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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, Inorganic & Nuclear
Babulal Maji, Anirban Bhandari, Rayantan Sadhukhan, Joyanta Choudhury
Summary: In this study, water-soluble Ru-NHC complexes were synthesized and tested for their catalytic activity in the transfer hydrogenation of quinoline-type N-heteroarenes using a formic acid/sodium formate buffer solution. The designed ligand within the catalyst backbone exhibited excellent durability, reusability, and compatibility with aqueous-phase operation. The catalytic system demonstrated high efficiency with as little as 0.25 mol% catalyst, providing an overall turnover number of approximately 900.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Zhaofeng Gao, Jingwen Liu, Haizhou Huang, Huiling Geng, Mingxin Chang
Summary: The research reports on efforts to merge two asymmetric reductive amination reactions into a single-step transformation, utilizing specific catalyst and acid additives to successfully synthesize enantiopure secondary amine products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tobias Wagener, Lukas Lueckemeier, Constantin G. Daniliuc, Frank Glorius
Summary: This study successfully demonstrates the synthesis of sought-after, enantioenriched delta-lactams through an interrupted hydrogenation mechanism using oxazolidinone-substituted pyridines and water.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Nanhua Luo, Hongling Shui, Yuhong Zhong, Jiuzhong Huang, Renshi Luo
Summary: This study presents an efficient and environmentally friendly method for synthesizing functionalized quinolines from 2-aminobenzyl alcohols and alpha,beta-unsaturated ketones. The research results demonstrate that alkali is essential for the high selectivities of this catalytic system.
SYNTHESIS-STUTTGART
(2021)
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.
Article
Chemistry, Physical
Huanhuan Jia, Rong Xie, Guangpeng Lu, Huanfeng Jiang, Min Zhang
Summary: In this study, we developed a hierarchically porous ZrO2-supported iridium catalyst derived from MOF, which exhibits sufficient accessible catalytic sites. This catalyst was successfully used for the selective and direct construction of julolidines via catalytic reductive annulation. It shows good substrate and functional group compatibility, can be reused, has high step and atom efficiency, and is easy to apply for the fabrication of functional molecules.
Article
Chemistry, Organic
Fabien Gelat, Stephane Lebrun, Natacha Henry, Francine Agbossou-Niedercorn, Christophe Michon, Eric Deniau
Article
Chemistry, Organic
Yann Corre, Vincent Rysak, Xavier Trivelli, Francine Agbossou-Niedercorn, Christophe Michon
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Review
Chemistry, Multidisciplinary
C. Dussenne, T. Delaunay, V. Wiatz, H. Wyart, I. Suisse, M. Sauthier
Article
Chemistry, Inorganic & Nuclear
Christophe Michon, Marc-Antoine Abadie, Florian Medina, Francine Agbossou-Niedercorn
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Romain Sallio, Stephane Lebrun, Frederic Capet, Francine Agbossou-Niedercorn, Christophe Michon, Eric Deniau
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Physical
Vincent Rysak, Armel Descamps-Mandine, Pardis Simon, Florent Blanchard, Laurence Burylo, Martine Trentesaux, Maxence Vandewalle, Vincent Colliere, Francine Agbossou-Niedercorn, Christophe Michon
CATALYSIS SCIENCE & TECHNOLOGY
(2018)
Article
Chemistry, Multidisciplinary
Emma Wilson, Clement Dumont, Mathieu Drelon, Isabelle Suisse, Christophe Penverne, Mathieu Sauthier
Article
Chemistry, Organic
Yann Corre, Vincent Rysak, Marton Nagyhazi, Dorottya Kalocsai, Xavier Trivelli, Jean-Pierre Djukic, Francine Agbossou-Niedercorn, Christophe Michon
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Crystallography
Yasmina Homrani, Abdelaziz Dahdouh, Mohamed Amin El Amrani, Pauline Loxq, Frederic Capet, Isabelle Suisse, Mathieu Sauthier
Summary: A dinuclear nickel complex with (S)-limonene based aminooxime ligand has been isolated and its crystal structure determined. The structure features two NiII ions coordinated in a distorted octahedral environment, with each oxime ligand forming two five-membered chelate rings. Numerous intermolecular and intramolecular hydrogen bonds in the crystal result in the formation of a three-dimensional network structure.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Reshma Kokane, Yann Corre, Erhard Kemnitz, Mohan K. Dongare, Francine Agbossou-Niedercorn, Christophe Michon, Shubhangi B. Umbarkar
Summary: The Pd/MgF2-x(OH)(x) palladium catalyst supported on acidic fluorinated magnesium hydroxide exhibited good catalytic activity in hydrogenation reactions, with the support's acid sites playing a key role in pre-activating N-heterocycle substrates. Additionally, the catalyst showed high recyclability up to 10 times without loss of activity or palladium leaching.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Physical
Vincent Rysak, Ruchi Dixit, Xavier Trivelli, Nicolas Merle, Francine Agbossou-Niedercorn, Kumar Vanka, Christophe Michon
CATALYSIS SCIENCE & TECHNOLOGY
(2020)
Article
Chemistry, Organic
Christophe Michon, Joachim Gilbert, Xavier Trivelli, Fady Nahra, Catherine S. J. Cazin, Francine Agbossou-Niedercorn, Steven P. Nolan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Biotechnology & Applied Microbiology
Vincent Rysak, Yann Corre, Francine Agbossou-Niedercorn, Christophe Michon
CHIMICA OGGI-CHEMISTRY TODAY
(2017)
Article
Chemistry, Multidisciplinary
Marc-Antoine Abadie, Xavier Trivelli, Florian Medina, Nathalie Duhal, Mostafa Kouach, Bernhard Linden, Eric Genin, Maxence Vandewalle, Frederic Capet, Pascal Roussel, Iker Del Rosal, Laurent Maron, Francine Agbossou-Niedercorn, Christophe Michon
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Physical
Yann Corre, Xavier Trivelli, Frederic Capet, Jean-Pierre Djukic, Francine Agbossou-Niedercorn, Christophe Michon
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
