Article
Chemistry, Multidisciplinary
Damiano Cirri, Tiziano Marzo, Alessandro Pratesi
Summary: This article describes an unprecedented palladium/arsenic-based catalytic cycle for the hydration of nitriles to amides, which takes place under exceptionally mild conditions of neutral pH and moderate temperature (60°C). The versatility of this new catalytic cycle was tested on various nitriles, ranging from aliphatic to aromatic. The effect of ring substitution with electron withdrawing and electron donating groups, as well as potentially interferent functional groups such as hydroxy or pyridinic nitrogen, was investigated. Furthermore, a pilot study on the potential scalability of this approach for industrial production is presented, demonstrating its potential and rapid scale-up capability.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Gauravjyoti D. Kalita, Podma P. Sarmah, Golap Kalita, Pankaj Das
Summary: A facile ligand-assisted approach was used to synthesize bimetallic Au-Pd nanoparticles with a tunable core@shell structure. The Au-Pd materials exhibited superior performance in two important reactions, with the Pd-core-Au-shell structure showing higher activity compared to the Au-core-Pd-shell structure.
NANOSCALE ADVANCES
(2021)
Article
Multidisciplinary Sciences
Luis Bering, Elliott J. Craven, Stanley A. Sowerby Thomas, Sarah A. Shepherd, Jason Micklefield
Summary: Amides are essential chemical bonds in nature and commonly found in proteins, metabolites, and synthetic products. This study presents an integrated multi-catalytic system that combines nitrile hydratase enzymes with a Cu-catalysed N-arylation reaction for the synthesis of amide bonds. The method offers high substrate loading, broad applicability, and excellent functional group tolerance, enabling the efficient synthesis of natural product derivatives, drug molecules, and challenging chiral amides under environmentally friendly conditions.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Perla Ramesh, Chinnabattigalla Sreenivasulu, Dakoju Ravi Kishore, Dasari Srinivas, Koteswara Rao Gorantla, Bhabani S. Mallik, Gedu Satyanarayana
Summary: This article describes the development of a new aliphatic nitrile-template-directed remote meta-selective C-H olefin functionalization reaction of arenes. The method is feasible at room temperature and enables the formation of products with excellent regioselectivity. The efficacy and robustness of the method have been demonstrated through the synthesis of various drug analogues and gram-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Birgit Grill, Melissa Horvat, Helmut Schwab, Ralf Gross, Kai Donsbach, Margit Winkler
Summary: This study describes the enantioselective preparation of the levetiracetam precursor using enzymatic dynamic kinetic resolution. By evaluating the iron-dependent nitrile hydratase from Gordonia hydrophobica, the potential for formation of the product in enantioenriched form was explored, along with its activity for the hydration of other nitriles. The substrate concentrations, reaction pH, and biocatalyst amount were found to significantly influence the yield and enantiomeric excess of the product.
Article
Chemistry, Multidisciplinary
Zhongxu Guo, Zhongtian Du, Yanbin Zhao, Xiaoyu Shen, Changhai Liang
Summary: This study presents a new approach for the selective hydration of nitriles using vanadium-nitrogen-carbon materials as catalysts. Compounds with different N and O atoms were found to have a significant impact on the reaction. This work expands the application of non-precious metal catalysts for nitrile hydration reactions.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Muhammad Asif Hussain, Eun Ju Choi, Adnan Maqbool, Muhammad Atif, Hassan Zeb, JaeGoo Yeo, Jung-A Yu, Yong-Hun Cho, Moses Noh, Jung Won Kim
Summary: A facile eco-friendly heterogeneous catalytic system has been developed for amide synthesis using Ru/MnO2 catalyst in water, showing outstanding activity for a wide range of nitriles and tolerance for heteroatom-containing nitriles. Pharmaceutically important compounds have been synthesized with appreciable yields and selectivities. The catalyst can be reused multiple times, demonstrating a green and technologically acceptable protocol.
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY
(2021)
Article
Chemistry, Organic
Masahiro Abe, Sayasa Nitta, Erina Miura, Tetsutaro Kimachi, Kiyofumi Inamoto
Summary: Herein, we present a simple method for the synthesis of nitriles via base-promoted intramolecular nucleophilic aromatic substitution. This process eliminates the need for toxic cyanide species and transition metals, while maintaining redox-neutral conditions. Our method demonstrates excellent scope and compatibility with various functional groups, resulting in good to excellent yields of (hetero)aromatic nitriles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Leyi Zhang, Shiyue Zhao, Cheng Chang, Jianan Wang, Chen Yang, Zhongyi Cheng
Summary: By redesigning the structure of a thermophilic nitrile hydratase, its catalytic activity and thermostability were improved under high acrylamide concentrations. Through structural analysis and simulations, specific amino acid residues were identified to be responsible for enhancing resistance to high acrylamide concentrations. The modified enzyme showed increased activity, stability, and acrylamide concentration compared to the wild-type enzyme.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Physical
Jianghao Zhou, Jing Guo, Alexander Moiseevich Mebel, Govinda Ghimire, Feng Liang, Shuai Chang, Jin He
Summary: Investigated the dehydration reaction of primary amides in visible-light driven self-assembled gold nanoparticle-aromatic primary amide-gold nanoelectrode junctions. Used time-resolved surface enhanced Raman spectroscopy (SERS) to study the reaction dynamics and intermediates, revealing the role of gold surface adatoms and picocavities in stabilizing and amplifying the intermediates.
Article
Chemistry, Multidisciplinary
Suranjana Chakrabarty, Anup Ghosh
Summary: Using infrared spectroscopy and density functional theory (DFT) calculations, we investigated the interactions between amide 1 and phenol derivatives (para-chlorophenol (PCP) and para-cresol (CP)). We found that amide I was involved in vibrational coupling with symmetric and asymmetric CC modes of different phenolic derivatives, and this coupling varied with different guest aromatic phenolic compounds. Substituting phenol affected the pattern of vibrational coupling with amide I. The symmetric and asymmetric CC modes of PC were significantly coupled with amide 1, while for PCP, the symmetric CC mode had significant coupling but the asymmetric mode had negligible coupling with amide I. Our findings provide valuable insights into the nature of vibrational coupling and its dependency on different factors.
Article
Chemistry, Physical
Yushan Yang, Shaoyu Yuan, Heli Pan, Zixuan Li, Zejiang Li, Sufang Sun, Yongjun Gao
Summary: A novel explosion-assistant strategy was developed to fabricate graphene oxide supported nickel and palladium three-component catalyst for hydrogenation of nitriles to secondary amines. The explosion during the synthesis of the catalyst was essential for the well-dispersion of palladium and the decomposition of metal salt precursors. The special structure of the catalyst facilitated the spillover of active hydrogen species, enhancing the catalytic activity.
APPLIED CATALYSIS A-GENERAL
(2022)
Article
Chemistry, Multidisciplinary
Sumit Kumar, Ramesh Ambatwar, Gopal L. Khatik
Summary: Aryl amides and amide derivatives are crucial functionalities in drug development, but their synthesis typically involves tedious or costly approaches such as amine condensation or coupling. This study presents two convenient methods for directly synthesizing aryl amides from aryl nitriles in a short time with high yields, utilizing base-driven partial hydrolysis.
RESEARCH ON CHEMICAL INTERMEDIATES
(2023)
Article
Chemistry, Physical
Yang Long, Yanling Zheng, Ying Xia, Lang Qu, Yuhe Yang, Haifeng Xiang, Xiangge Zhou
Summary: A nickel-catalyzed synthesis of aryl nitriles via aryl exchange has been developed. The reaction utilizes cheap and easily handled 4-cyanopyridine as the cyanating source, allowing for the efficient conversion of various aromatic amides into aryl nitriles. The reaction exhibits wide substrate scope, good selectivity, and is complementary to traditional methods. Additionally, the mechanism is supported by the determination of two key nickel complexes through X-ray crystallography.
Article
Chemistry, Physical
Sara Gomez, Cettina Bottari, Franco Egidi, Tommaso Giovannini, Barbara Rossi, Chiara Cappelli
Summary: This study investigates the origin of the unique amide spectral features of proteins in aqueous solution using a combined theoretical and experimental approach. By comparing UVRR spectra recorded at different excitation wavelengths and modeled using a polarizable QM/MM approach, the study demonstrates the crucial role of specific hydrogen bond interactions in the selective enhancement of amide signals. These results further highlight the potential of vibrational spectroscopy methods for refined structural analysis of peptides and proteins in aqueous solution.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
