Article
Chemistry, Multidisciplinary
J. Daniel Bailey, Edward Helbling, Amey Mankar, Matthew Stirling, Fred Hicks, David K. Leahy
Summary: Reducing or eliminating organic solvent use in pharmaceutical manufacturing is a highly effective way to reduce environmental, health, and safety impacts. The process described utilizing primarily water-based methods significantly reduces material inputs and organic solvent use, while surprisingly using less water and improving overall yield compared to traditional methods.
Article
Chemistry, Physical
Itziar Penafiel, Robert A. W. Dryfe, Nicholas J. Turner, Michael F. Greaney
Summary: The integration of electro and bio-catalysis offers new ways of making molecules under very mild, environmentally benign conditions. The combined process offers a new approach to amine alkylation with native alcohols, a key bond formation in the chemical economy that is currently achieved via precious metal-catalyzed hydrogen-borrowing technologies.
Article
Chemistry, Multidisciplinary
Chenglong Dong, Yushan Wu, Hongtao Wang, Jiebang Peng, Yanzhi Li, Chanatip Samart, Mingyue Ding
Summary: The research reported the use of Ni nanoparticles supported on gamma-Al2O3 as a highly active catalyst for the synthesis of primary amines, showing excellent selectivity and high yields. Compared to precious metal catalysts, the Ni/Al2O3 catalyst demonstrated superior efficiency and sustainability for industrial production of amines.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Jade Dussart-Gautheret, Julie Yu, Krithika Ganesh, Gaikwad Rajendra, Fabrice Gallou, Bruce H. Lipshutz
Summary: This study describes the surfactant-enabled asymmetric ATA-catalyzed reductive aminations in water, which enhance the conversion levels and enable 1-pot chemoenzymatic catalysis. The modified conditions involving both biocatalysis and chemocatalysis are environmentally responsible, indicating the potential of using chemistry in water.
Article
Chemistry, Multidisciplinary
Matthias Elfinger, Timon Schoenauer, Sabrina L. J. Thomae, Robert Staeglich, Markus Drechsler, Mirijam Zobel, Juergen Senker, Rhett Kempe
Summary: The 3D metal catalyst developed here utilizes hydrogen as the reducing agent and easily handled ammonia dissolved in water as the nitrogen source for the synthesis of primary amines. The catalyst operates under mild conditions and outperforms commercially available noble metal catalysts. The key to its high activity is the unique support material it uses.
Article
Chemistry, Multidisciplinary
Mujeeb A. Sultan, Renjith Raveendran Pillai, Eman Alzahrani, Ahmed A. Alsofi, Sadam A. Al-Qadhi, Rami Adel Pashameah
Summary: In this study, a maprotiline analog was synthesized and its structure was elucidated using NMR and mass spectrometry techniques. Density functional theory calculations and molecular docking simulations showed that the synthesized compounds have good antidepressant activities, making them potential candidates for antidepressant drugs.
JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Hao Song, Yao Xiao, Zhuohua Zhang, Wanjin Xiong, Ren Wang, Liangcheng Guo, Taigang Zhou
Summary: A new synthetic method for the selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines has been developed. The method demonstrates high selectivity and yields up to 95%, and has been successfully applied in the synthesis of N-15 labeled compounds with an 89% yield.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Matthias Elfinger, Christof Bauer, Joerg Schmauch, Michael Moritz, Christoph Wichmann, Christian Papp, Rhett Kempe
Summary: This study presents an efficient method for the selective synthesis of differently substituted primary, secondary, and tertiary alkyl amines by combining borrowing hydrogen or hydrogen autotransfer and reductive amination with hydrogen. A nanostructured, bimetallic Co/Sc catalyst is used to mediate both reactions efficiently. The method shows broad product scope, good functional group tolerance, easy upscaling, and catalyst reusability.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Xinmin Li, Yue Hu, Asma M. Alenad, Bei Zhou, Zhuang Ma, Jie Gao, Rajenahally V. Jagadeesh, Matthias Beller
Summary: A mild and convenient protocol for the synthesis of diverse secondary and tertiary amines, as well as N-methylated products, is presented. This protocol works efficiently at room temperature using ammonia borane as the reductant and is applicable to a wide range of substrates, including chiral amines and amino acid derivatives. The utility of this methodology is demonstrated by gram-scale reactions and selected synthesis of drug molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Vinothkumar Vinayagam, Tanguturi Venkatanarayana Hajay Kumar, Ravi Nune, Satish Kumar Karre, Subir Kumar Sadhukhan
Summary: We developed a one-step procedure for selectively reducing secondary and tert-amides to their corresponding amine derivatives in the presence of an ester. This reaction was achieved by combining photoredox, nickel catalysis, and phenyl silane as a reductant under blue LED light (455 nm) at room temperature. Furthermore, this mild light-promoted dual metallaphotoredox catalytic system was effective in selectively reducing lactam to cyclic amines without affecting the ester moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Jeremy Steflik, Amelia Gilio, Michael Burns, Gideon Grogan, Rajesh Kumar, Russell Lewis, Carlos Martinez
Summary: This study reports a method for biocatalytic reductive amination reactions, which have high potential value in pharmaceutical synthesis. The researchers identified and engineered a RedAm enzyme to catalyze the synthesis of a key intermediate for a cyclin-dependent kinase (CDK) inhibitor. The optimized enzyme variant showed high productivity at high substrate concentrations (50-fold improvement over the wild-type). Crystal structures of both the wild-type and mutant enzymes were solved to elucidate the structural changes that improved the performance of the RedAm under process conditions. This work demonstrates the versatility and industrial utility of RedAm-catalyzed reductive amination by enabling the synthesis of a chiral intermediate on a multikilogram scale.
Article
Chemistry, Multidisciplinary
Iuliia Polishchuk, Jan Sklyaruk, Yury Lebedev, Magnus Rueping
Summary: Half-sandwich iridium complexes with bidentate urea-phosphorus ligands were found to catalyze the direct reductive amination of ketones with high selectivity under mild conditions. One of the complexes showed activity in two different reactions and the use of ammonium formate does not require special conditions, taking place in HFIP instead of methanol.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Applied
Laurine Ducrot, Megan Bennett, Gideon Grogan, Carine Vergne-Vaxelaire
Summary: The biocatalytic asymmetric synthesis of amines from carbonyl compounds and amine precursors represents a significant advancement in sustainable synthetic chemistry, offering advantages such as enhanced selectivity, stability, and substrate scope. Utilizing a combination of structure-informed protein engineering and natural genetic resources, various oxidoreductases have been identified to catalyze the reductive amination reaction. This approach demonstrates the potential for the industrial synthesis of chiral amines through the development of biocatalysts with improved activity and altered properties.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Da Ke, Shaodong Zhou
Summary: In this study, an efficient nickel boride nanoclusters catalyst supported by a TS-1 molecular sieve was reported for the synthesis of amines. The catalyst showed high activity, simple preparation, and reusability, making it promising for industrial production of amines.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Jun Zhang, Daohong Liao, Rongchang Chen, Fangfang Zhu, Yaqing Ma, Lei Gao, Ge Qu, Chengsen Cui, Zhoutong Sun, Xiaoguang Lei, Shu-Shan Gao
Summary: In this study, a concise strategy combining rational design and engineering techniques was developed to enhance the substrate scope and catalytic efficiency of imine reductases (IREDs). The variant M5 exhibited superior performance and broad substrate scope for the synthesis of diverse azacycloalkylamines. This study provides exciting opportunities in medicinal and process chemistry as well as synthetic biology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Duo Wei, Vincent Dorcet, Christophe Darcel, Jean-Baptiste Sortais
Article
Chemistry, Multidisciplinary
Ruqaya Buhaibeh, Oleg A. Filippov, Antoine Bruneau-Voisine, Jeremy Willot, Carine Duhayon, Dmitry A. Valyaev, Noel Lugan, Yves Canac, Jean-Baptiste Sortais
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Physical
Duo Wei, Antoine Bruneau-Voisine, Maxime Dubois, Stephanie Bastin, Jean-Baptiste Sortais
Article
Chemistry, Organic
Duo Wei, Ruqaya Buhaibeh, Yves Canac, Jean-Baptiste Sortais
Editorial Material
Chemistry, Physical
Lutz Ackermann, Jean-Baptiste Sortais
Article
Chemistry, Physical
Karim Azouzi, Antoine Bruneau-Voisine, Laure Vendier, Jean-Baptiste Sortais, Stephanie Bastin
CATALYSIS COMMUNICATIONS
(2020)
Article
Chemistry, Inorganic & Nuclear
Ruqaya Buhaibeh, Carine Duhayon, Dmitry A. Valyaev, Jean-Baptiste Sortais, Yves Canac
Summary: The coordination chemistry of NHC core pincer-type PCP and PCN ligands with a Mn(I) center was studied, revealing that Mn(I) complexes with bidentate and tridentate ligands exhibit different catalytic activities based on ligand structure.
Article
Chemistry, Inorganic & Nuclear
Alina A. Grineva, Oleg A. Filippov, Yves Canac, Jean-Baptiste Sortais, Sergei E. Nefedov, Noel Lugan, Vincent Cesar, Dmitry A. Valyaev
Summary: The study involved lithiation and transmetalation to prepare a heterobimetallic complex with an anionic ditopic imidazol-2,4-diylidene ligand, which was further converted to a bis(iron) complex with metalated carbenic groups. It was found that metalation significantly affects the electronic donation properties of the ligand.
INORGANIC CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Duo Wei, Ruqaya Buhaibeh, Yves Canac, Jean-Baptiste Sortais
Summary: This review summarizes the development of rhenium-based catalysts for hydrosilylation reactions of various functional groups and their mechanisms. The importance of hydrosilylation in both the silicon industry and fine chemistry is highlighted.
Article
Chemistry, Multidisciplinary
Karim Azouzi, Dmitry A. Valyaev, Stephanie Bastin, Jean-Baptiste Sortais
Summary: This review comprehensively covers transfer hydrogenation processes catalyzed by manganese organometallic complexes, with a focus on reduction reactions of various substances and ligand design for Mn-catalyzed asymmetric transfer hydrogenation reactions.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2021)
Review
Chemistry, Inorganic & Nuclear
Ekaterina S. Gulyaeva, Elena S. Osipova, Ruqaya Buhaibeh, Yves Canac, Jean-Baptiste Sortais, Dmitry A. Valyaev
Summary: This paper provides a comprehensive review of the rapidly emerging application of organometallic manganese complexes in catalytic reactions. It focuses on the influence of different donor ligands on catalytic activity and selectivity, the comparison with polydentate systems, and the study of mechanistic aspects.
COORDINATION CHEMISTRY REVIEWS
(2022)
Article
Chemistry, Inorganic & Nuclear
Karim Azouzi, Lucie Pedussaut, Romane Pointis, Anna Bonfiglio, Riddhi Kumari Riddhi, Carine Duhayon, Stephanie Bastin, Jean-Baptiste Sortais
Summary: Manganese, an earth-abundant transition metal, shows great potential as a catalyst for reduction-type reactions. In this study, a simple bis-N-heterocyclic ligand without phosphine associated with manganese complex [Mn(bis-NHCMes)(CO)(3)Br] was found to effectively catalyze the hydrogenation of carboxylic esters in the presence of KBHEt(3) as an activator at high temperature and pressure.
Article
Chemistry, Multidisciplinary
Duo Wei, Ruqaya Buhaibeh, Yves Canac, Jean-Baptiste Sortais
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Nikolay Kireev, Oleg A. Filippov, Ekaterina S. Gulyaeva, Elena S. Shubina, Laure Vendier, Yves Canac, Jean-Baptiste Sortais, Noel Lugan, Dmitry A. Valyaev
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Antoine Bruneau-Voisine, Lenka Pallova, Stephanie Bastin, Vincent Cesar, Jean-Baptiste Sortais
CHEMICAL COMMUNICATIONS
(2019)
