Review
Chemistry, Multidisciplinary
Max Lubberink, William Finnigan, Sabine L. Flitsch
Summary: Amide bonds are commonly formed in the pharmaceutical industry and there is a growing interest in biocatalytic methods for their synthesis. The use of low water systems and ATP-dependent enzymes have shown promise in driving amide bond formation. A publicly available database, RetroBioCat, has been compiled to provide literature on these methods.
Review
Chemistry, Multidisciplinary
Jitender Singh, Anuj Sharma
Summary: The amide bond is a fascinating functional group in nature, known for its stability, conformational diversity, high polarity, and abundance in natural products and drug candidates. Traditional methods for synthesizing amides are time-consuming and generate substantial waste, making them environmentally and economically burdensome. In recent years, visible light-mediated methods have emerged as a mild and environmentally friendly approach for the synthesis of amides, attracting significant attention in research.
NEW JOURNAL OF CHEMISTRY
(2022)
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)
Article
Chemistry, Physical
Sara Gomez, Cettina Bottari, Franco Egidi, Tommaso Giovannini, Barbara Rossi, Chiara Cappelli
Summary: The origin of the specific amide spectral features of proteins in aqueous solution were investigated through a combined theoretical and experimental approach. Results demonstrated the crucial role of specific hydrogen bond interactions in the selective enhancement of amide signals. These findings further highlight the value of vibrational spectroscopy methods for refined structural analysis of peptides and proteins in aqueous solution.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Applied
Sofia Strekalova, Alexander Kononov, Vladimir Morozov, Olga Babaeva, Elena Gavrilova, Yulia Budnikova
Summary: This study describes the electrochemical amidation of C(sp2)-H and C(sp3)-H bonds of a wide range of arenes using nitriles as amide sources, achieved under mild conditions without the need for metal catalysts or external oxidizing agents. The method offers moderate to high yields, can be applied to arenes with diverse functional groups, and is suitable for gram scale synthesis. The key role of the hydroxyl radical as an inductor generated during the oxidation of water has been established through EPR experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Applied
Paola Acosta-Guzman, Andrea Ojeda-Porras, Diego Gamba-Sanchez
Summary: The construction of amide bonds is of great interest due to their prevalence in bioactive molecules. This review presents the most viable strategies for constructing amide bonds, with a focus on recent developments in the field.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Luca Marius Grossmann, Vera Beier, Lea Duttenhofer, Laura Lennartz, Till Opatz
Summary: Amide bonds are commonly found in natural products and pharmaceuticals. While various methods exist for their formation, classical activating reagents can still pose challenges. Developing more sustainable methods is highly desirable.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Editorial Material
Chemistry, Multidisciplinary
Luca Marius Grossmann, Vera Beier, Lea Duttenhofer, Laura Lennartz, Till Opatz
Summary: The cover of this issue features the electrochemical coupling of amines and carboxylic acids to form amides.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Materials Science, Multidisciplinary
Jun Yang, Yunxia Ping, Wei Liu, Wenjie Yu, Zhongying Xue, Xing Wei, Aimin Wu, Bo Zhang
Summary: The study investigates the reactions between nickel and germanium by incorporating a titanium interlayer, with the best quality nickel germanide achieved through microwave annealing at 350 degrees C. The titanium interlayer acts as a cap layer after annealing, facilitating the uniform formation of nickel germanide layer at low microwave annealing temperatures.
Article
Chemistry, Applied
Debora Procopio, Xavier Marset, Gabriela Guillena, Maria Luisa Di Gioia, Diego J. Ramon
Summary: In this study, environmentally friendly deep eutectic solvents (DESs) were used for the first time as reaction media for efficient photocatalytic amide synthesis at room temperature. The method showed mild conditions, a broad substrate scope, high yields (& LE;99%), and tolerance to air and moisture. It also allowed for the recycling of the reaction medium and catalyst without significant decrease in yield for at least three consecutive cycles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Biochemistry & Molecular Biology
Bin Lu, Wen-Jing Xiao, Jia-Rong Chen
Summary: Visible-light photoredox catalysis has gained significant attention in the synthetic community due to its potential for sustainable and efficient activation of organic molecules. Amide synthesis through photoredox catalysis has become increasingly popular as it allows for the preparation of a wide variety of amides from halides, arenes, and alkanes using visible light irradiation. These methods offer an alternative to traditional amide synthesis strategies involving stoichiometric activating agents.
Article
Chemistry, Physical
Nuria Martin, Francisco G. Cirujano
Summary: The direct synthesis of amides from carboxylic acids and amines is of great importance in fine chemistry, drug synthesis, and protein construction in living organisms. The use of heterogeneous catalysts is preferred due to their advantages in terms of easy isolation, recovery, and recycling. This article reviews the most relevant reported heterogeneous catalysts for direct amide bond formation, focusing on their physicochemical properties, catalytic performance, and understanding of the reaction mechanism. The types of active sites incorporated on the solid catalyst surface, their interplay with the support material, and key properties such as surface area and pore size are thoroughly discussed.
CATALYSIS COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Changxu Zhong, Shaowei Wang, Ping Lu
Summary: This report introduces a practical strategy to access enantioenriched cyclobutenes through chiral lithium amide mediated deprotonation of 3-substituted cyclobutanones. Moreover, this strategy has been successfully applied to synthesize protoilludane analogues via a sequential Negishi coupling of enol phosphates and Diels-Alder reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Astronomy & Astrophysics
Ivan Petukhov, Anastasia Petukhova, Stanislav Petukhov
Summary: We propose a model for the injection of solar energetic particles into interplanetary space during gradual events, with particle acceleration taking place in a confined region of the solar atmosphere. We calculate the distribution function for particles accelerated by diffusion mechanism and determine the flux of injected particles as a function of time and energy. We provide an explanation for the characteristic properties of the injection function and their dependence on particle energy. Comparisons with ground-based measurements during the 2001 April 15 event show rough agreement with particle density over time and good agreement with the spectrum of maximum intensity values.
ASTROPHYSICAL JOURNAL
(2023)
Article
Chemistry, Organic
Yiping Li, Jingyue Li, Guangjun Bao, Changjun Yu, Yuyang Liu, Zeyuan He, Peng Wang, Wen Ma, Junqiu Xie, Wangsheng Sun, Rui Wang
Summary: In this study, a novel coupling reagent NDTP was explored, which exhibited mild, nonirritating, convenient availability, and recyclability. It could activate carboxylic acids via acyl thiocyanide and enable the rapid synthesis of amides and peptides under mild conditions. Furthermore, the methodology was compatible with Fmoc-SPPS, providing an alternative approach for peptide manufacturing.
Article
Chemistry, Organic
David Bernier, Alexander J. Blake, Simon Woodward
JOURNAL OF ORGANIC CHEMISTRY
(2008)
Review
Chemistry, Organic
David Bernier, Ulrike K. Wefelscheid, Simon Woodward
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
(2009)
Article
Chemistry, Organic
Laura Santos, Armen Panossian, Morgan Donnard, Jean-Pierre Vors, Sergii Pazenok, David Bernier, Frederic R. Leroux
Article
Chemistry, Organic
Laura Santos, Morgan Donnard, Armen Panossian, Jean-Pierre Vors, Peter Jeschke, David Bernier, Sergii Pazenok, Frederic R. Leroux
Summary: The N-alkylation of imino-thiazolidinones, which are ambident and weakly nucleophilic, has been achieved through substitution with alkyl fluorosulfonates. These reactive electrophiles are obtained by transforming non-toxic, economic, and commercially available alcohol derivatives with SO2F2 gas. The use of electron-withdrawing groups and DMAc as a solvent allows for a (Z)- and N-endocyclic selectivity in the introduction of various alkyl and polyfluoroalkyl chains.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Clotilde Placais, Morgan Donnard, Armen Panossian, Jean-Pierre Vors, David Bernier, Sergii Pazenok, Frederic R. Leroux
Summary: A rapid and simple synthesis method has been developed to access rarely described 3-amino-5-fluoroalkylfurans by cyclization of easily accessible fluorovinamides. The method is compatible with four different fluorinated groups and a wide range of substituents on the amine, affording the desired furans as hydrochloride salts in quantitative or nearly quantitative yields.
Article
Chemistry, Organic
Axel Sabourin, Jeremy Dufour, Jean-Pierre Vors, David Bernier, Jean-Luc Montchamp
Summary: Various approaches for the preparation of phosphorus-substituted 5- and 6-membered benzophostams are discussed in the text, including carbodiimide-promoted cyclization and copper-catalyzed cross-coupling reactions. The methods for synthesizing P-ethoxy-substituted 5-membered benzophostams are compared in the study.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Axel Sabourin, Jeremy Dufour, Jean-Pierre Vors, David Bernier, Jean-Luc Montchamp
Summary: This study presents the synthesis of N- and C-substituted benzophostams. N-substitution was achieved by alkylation using a heterocycle, LiHMDS, and alkyl halide, or by copper-catalyzed cyclization of N-alkyl phosphonamide. N-Arylation could be accomplished either on the preformed heterocycle or on the phosphonamide precursor via copper-catalyzed cross-coupling. Dimethylation at the benzylic position was conducted using LiHMDS and methyl iodide, or a palladium-catalyzed reductive Heck reaction as a cost-effective and efficient alternative.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Laura Santos, Florian Audet, Morgan Donnard, Armen Panossian, Jean-Pierre Vors, David Bernier, Sergii Pazenok, Frederic R. Leroux
Summary: An efficient method for the synthesis of high-value N-polyfluoroalkyl anilines, primary polyfluoroalkylamines, and N,N-bis(polyfluoroalkyl) amines via N-polyfluoroalkylation of sulfonamides and phthalimide derivatives using sulfuryl fluoride (SO2F2) is reported. The in situ formation of polyfluoroalkyl fluorosulfonates from commercially available fluorinated alcohols and economical sulfuryl fluoride is advantageous in terms of environmental impact and cost. This general method allows for the polyfluoroalkylation of a variety of substrates, providing valuable building blocks for life science applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Clotilde Placais, Sherif J. Kaldas, Morgan Donnard, Armen Panossian, David Bernier, Sergii Pazenok, Frederic R. Leroux
Summary: This work presents the synthesis of aryl and alkenyl halides from fluorosulfonates using commercially available ruthenium catalysts. It is the first study to efficiently convert phenols to aryl halides with chloride, bromide, and iodide. Fluorosulfonates can be easily prepared using sulfuryl fluoride (SO2F2) and cost-effective substitutes for triflates. Additionally, this work also reports an efficient coupling of alkenyl fluorosulfonates for the first time. Representative examples demonstrate that the reaction can be carried out in a one-pot process, starting directly from phenol or aldehyde.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Meeting Abstract
Chemistry, Multidisciplinary
Stefan Lehr, David Bernier, Thomas Droege, Marc Mosrin, Jullien Rey, Joerg Tiebes
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Meeting Abstract
Chemistry, Multidisciplinary
David Bernier, Pierre-Yves Coqueron, Christophe Dubost, Anne-Sophie Rebstock
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Correction
Chemistry, Organic
David Bernier, Reinhard Brueckner
SYNTHESIS-STUTTGART
(2009)
Article
Chemistry, Organic
David Bernier, Frank Moser, Reinhard Brueckner
SYNTHESIS-STUTTGART
(2007)
Article
Chemistry, Organic
David Bernier, Reinhard Brueckner
SYNTHESIS-STUTTGART
(2007)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
