Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Chisa Takahara, Masashi Nakamura, Yuto Aoyama, Takumi Yanagihara, Shunichiro Ito, Kazuo Tanaka, Hiroaki Imoto, Kensuke Naka
Summary: Arsenic-containing conjugated polymers have gained significant attention recently. To improve solubility in organic solvents, long alkyl chains are commonly introduced on the coupling partner and/or at the 3-positions of fused thiophene rings in traditional polymer design. However, this strategy is not applicable for comonomers with difficulties in alkyl group substitution, and the steric hindrance of alkyl chains can distort the planarity of polymer chains. Therefore, a novel monomer with an alkoxyphenyl group substituted on the arsenic atom was developed. By using benzothiadiazole and benzoxadiazole monomers, polymers with high planarity and solubility were developed, exhibiting near-infrared emissions.
Article
Polymer Science
Chisa Takahara, Masashi Nakamura, Yuto Aoyama, Takumi Yanagihara, Shunichiro Ito, Kazuo Tanaka, Hiroaki Imoto, Kensuke Naka
Summary: Arsenic-containing conjugated polymers, with dithieno[3,2-b:2',3'-d]arsole as a typical monomer unit, have gained significant attention recently. However, the traditional polymer design for improved solubility often involves introducing long alkyl chains, which may lead to steric hindrance and distort the planarity of the polymer chain. To overcome this, a novel monomer with an alkoxyphenyl group substituted on the arsenic atom was developed. These polymers, using benzothiadiazole and benzoxadiazole monomers, exhibited high planarity and solubility, as well as near-infrared emissions.
Article
Chemistry, Multidisciplinary
Miki B. Kurosawa, Kenta Kato, Kei Muto, Junichiro Yamaguchi
Summary: A deoxygenative transformation method was developed for the synthesis of multiply arylated alkanes from various diarylketones. The method involves a phospha-Brook rearrangement of diarylketones by reacting with diphenylphosphine oxide, followed by palladium-catalyzed cross-couplings or a Friedel-Crafts type alkylation. The method also enables the one-pot conversion from arylcarboxylic acids to diarylmethanes and tetraarylethanes, as well as the synthesis of tetraarylmethane and triphenylethane using sequential coupling reactions.
Review
Chemistry, Multidisciplinary
Anna-Carin C. Carlsson, Staffan Karlsson, Rachel H. Munday, Matthew R. . Tatton
Summary: Atropisomerism is a stereochemical phenomenon exhibited by molecules with a rotationally restricted sigma bond. Atropisomers exist as a dynamic mixture and can be interconverted without breaking and reforming bonds. They are frequent targets in medicinal chemistry projects due to their axial chirality and unique 3D structures. However, selecting a single atropisomer presents problems such as interconversion and separation challenges. Chromatography, enzymatic or chiral catalysts can be used for separation, but each method has limitations. This Account discusses the successes, failures, and challenges of developing methods for resolution and synthesis of atropisomeric drug candidates.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Peng Xu, Xin Hong Duan
Summary: A greener and more practical strategy has been developed for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides, enabling the synthesis of specific C3-arylindoles in water. The method combines aqueous homogeneous catalysis and ligand mediation, allowing for a broad substrate scope and functional-group tolerance.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Feiyan Yang, Chuan Wang
Summary: In this study, we employ polycyclic aryl-activated alkyl ammonium triflates as the electrophilic aryl-activated alkylating agent in the nickel-catalyzed hydroxyl- or sulfonamide-directed cross-electrophile coupling reaction with phenyl benzoates, resulting in the synthesis of diverse aryl ketones under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, Paul J. Chirik
Summary: A cobalt-catalyzed method for the C(sp(2))-C(sp(3)) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides was developed, with cobalt-ligand combinations being assessed through high-throughput experimentation. The use of cobalt(II) sources with trans-N,N'-dimethylcyclohexane-1,2-diamine (DMCyDA, L-1) resulted in optimal yield and selectivity. The transformation allowed for diverse steric and electronic properties on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile, with radical trap experiments supporting the formation of electrophile-derived radicals during catalysis.
Article
Chemistry, Organic
Quan Lin, Hegui Gong, Fan Wu
Summary: Here, we present a nickel-catalyzed reductive coupling reaction of bromopyridines with tertiary alkyl bromides, enabling the synthesis of alkylated pyridines bearing an all-carbon quaternary center. This strategy offers mild conditions, a broad substrate scope, and high functional group tolerance. We believe this method provides an alternative solution to the challenging task of synthesizing sterically congested alkylpyridines, benefiting the synthetic community and pharmaceutical industry.
Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
Article
Chemistry, Physical
Savvas N. Georgiades, Persefoni G. Nicolaou, Nikos Panagiotou
Summary: This study demonstrates the successful synthesis of mono- and bis-phenyl derivatives of functionality-rich 2,6-diphenylpyrimidine substrates using a LED-activated, photoredox-mediated method. The phenylation at the ortho site(s) of the pyrimidine-C2-connected phenyl ring was found to be influenced by substituent-dependent electronic and steric effects. The generated library of derivatives shows promising features for evaluation in drug discovery efforts.
Article
Chemistry, Multidisciplinary
Pascal Hauk, Valerie Mazan, Fabrice Gallou, Joanna Wencel-Delord
Summary: This article reports the unexpected potential of micellar medium to achieve challenging beta-selective direct arylation of (oligo)thiophenes. By using a water/surfactant solution combined with natural feedstock-derived undecanoic acid as an additive, this high-yielding C-H coupling can be performed regioselectively at room temperature.
Article
Chemistry, Multidisciplinary
Jie Xu, Samantha Grosslight, Kyle A. Mack, Sierra C. Nguyen, Kyle Clagg, Ngiap-Kie Lim, Jacob C. Timmerman, Jeff Shen, Nicholas A. White, Lauren E. Sirois, Chong Han, Haiming Zhang, Matthew S. Sigman, Francis Gosselin
Summary: An efficient asymmetric synthesis of a potent KRAS G12C covalent inhibitor, GDC-6036, was reported. The synthesis involved a highly selective Negishi coupling and a series of reaction sequences, leading to the desired compound with a 40% overall yield from the starting materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Zahra Khorsandi, Abdol R. Hajipour, Mohamad Reza Sarfjoo, Rajender S. Varma
Summary: The nano-catalytic system described consists of magnetic nanoparticles as the core and edible natural ligands with functional groups as supports for cobalt species. It shows good catalytic activity in C-N cross-coupling reactions and demonstrates excellent efficiency and versatility in an array of coupling reactions. The system is easily accessible and has good recyclability for potential future applications.
Article
Chemistry, Organic
Jia-Sheng Ouyang, Xinhuan Zhang, Bendu Pan, Haobin Zou, Albert S. C. Chan, Liqin Qiu
Summary: A highly efficient and easy-to-operate solvent-free Buchwald-Hartwig amination method was developed using a robust N-heterocyclic carbene-palladium complex, with catalyst amount as low as 0.05 wt %. The method was successfully applied to the synthesis of commercial pharmaceuticals and candidate drugs with high yields.
Review
Chemistry, Organic
Vincent O. Hervin, Eloi P. Coutant, Glwadys Gagnot, Yves L. Janin
SYNTHESIS-STUTTGART
(2017)
Article
Oncology
Stephanie Arnould, Genevieve Rodier, Gisele Matar, Charles Vincent, Nelly Pirot, Yoann Delorme, Charlene Berthet, Yoan Buscail, Jean Yohan Noel, Simon Lachambre, Marta Jarlier, Florence Bernex, Helene Delpech, Pierre Olivier Vidalain, Yves L. Janin, Charles Theillet, Claude Sardet
Article
Chemistry, Organic
Eloi P. Coutant, Vincent Hervin, Glwadys Gagnot, Candice Ford, Racha Baatallah, Yves L. Janin
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Glwadys Gagnot, Vincent Hervin, Eloi P. Coutant, Sarah Desmons, Racha Baatallah, Victor Monnot, Yves L. Janin
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Eloi P. Coutant, Glwadys Gagnot, Vincent Hervin, Racha Baatallah, Sophie Goyard, Yves Jacob, Thierry Rosek, Yves L. Janin
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Multidisciplinary Sciences
Soon Gang Choi, Julien Olivet, Patricia Cassonnet, Pierre-Olivier Vidalain, Katja Lucks, Luke Lambourne, Kerstin Spirohn, Irma Lemmens, Melanie Dos Santos, Caroline Demeret, Louis Jones, Sudharshan Rangarajan, Wenting Bian, Eloi P. Coutant, Yves L. Janin, Sylvie van Der Werf, Philipp Trepte, Erich E. Wanke, Javier De Las Rivas, Jan Tavernier, Jean-Claude Twizere, Tong Hao, David E. Hill, Marc Vidal, Michael A. Calderwood, Yves Jacob
NATURE COMMUNICATIONS
(2019)
Article
Allergy
Sophie Goyard, Bianca Balbino, Rebecca S. Chinthrajah, Shu-Chen Lyu, Yves L. Janin, Pierre Bruhns, Pascal Poncet, Stephen J. Galli, Kari C. Nadeau, Laurent L. Reber, Thierry Rose
Article
Chemistry, Multidisciplinary
Glwadys Gagnot, Vincent Hervin, Eloi P. Coutant, Sophie Goyard, Yves Jacob, Thierry Rose, Fatima Ezzahra Hibti, Alessia Quatela, Yves L. Janin
Summary: This work focuses on the design and synthesis of luciferin analogues related to blue-hued coelenterazine, aiming to produce photons possibly at different wavelengths. Despite the presence of substituents found in actual substrates, no bioluminescence was observed with these compounds, however, they produced light signals through chemiluminescence in a phosphate buffer. The addition of a quaternary ammonium salt in the buffer increased the light signal intensity, contributing to the determination of emission spectra of these luciferin analogues.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Immunology
Francois Anna, Sophie Goyard, Ana Ines Lalanne, Fabien Nevo, Marion Gransagne, Philippe Souque, Delphine Louis, Veronique Gillon, Isabelle Turbiez, Francois-Clement Bidard, Aline Gobillion, Alexia Savignoni, Maude Guillot-Delost, Francois Dejardin, Evelyne Dufour, Stephane Petres, Odile Richard-Le Goff, Zaineb Choucha, Olivier Helynck, Yves L. Janin, Nicolas Escriou, Pierre Charneau, Franck Perez, Thierry Rose, Olivier Lantz
Summary: This study conducted in Paris conurbation found that the prevalence of SARS-CoV-2 infection in active workers was approximately 11.6% in May-July 2020, higher than laboratory testing positivity rates. The research also indicated that some infected individuals did not exhibit systemic IgG responses, suggesting that the true infection rate may have reached 16.6%, with anosmia and ageusia being common symptoms of infection.
EUROPEAN JOURNAL OF IMMUNOLOGY
(2021)
Article
Multidisciplinary Sciences
Juliette Fernandez, Cedric Hassen-Khodja, Virginie Georget, Thierry Rose, Yves Jacob, Yves L. Janin, Sebastien Nisole, Pierre-Olivier Vidalain, Nathalie J. Arhel
Summary: The recent emergence and reemergence of viruses in the human population has emphasized the necessity of developing broader panels of therapeutic molecules. High-throughput screening assays can identify innovative antiviral molecules by providing access to untargeted steps of the viral replication cycle. The development of an innovative protein complementation assay, named alpha Centauri, allows for the measurement of viral translocation between subcellular compartments, offering a robust readout of specific steps of viral infection in a multiwell format suitable for high-throughput screening.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2021)
Article
Chemistry, Organic
Glwadys Gagnot, Pierre Legrand, Amira Tadros, Fatima Ezzahra Hibti, Alessia Quatela, Yves L. Janin
Summary: Research on new chemiluminescent substances related to marine luciferin coelenterazine led to the synthesis of nitrogen-rich pyridopyrazine-bearing analogues, including the benzyl-bearing pyridopyrazinols. Challenges were faced in the synthesis of halogenated pyridopyrazines, with varying degrees of difficulties encountered. Despite these challenges, the target O-acetylated luciferin and its derivative were successfully prepared, with their chemiluminescence emission spectra determined.
SYNTHESIS-STUTTGART
(2021)
Article
Virology
Cyrille Mathieu, Franck Touret, Clemence Jacquemin, Yves L. Janin, Antoine Nougairede, Manon Brailly, Magalie Mazelier, Didier Decimo, Virginie Vasseur, Aymeric Hans, Jose-Carlos Valle-Casuso, Xavier de Lamballerie, Branka Horvat, Patrice Andre, Mustapha Si-Tahar, Vincent Lotteau, Pierre-Olivier Vidalain
Summary: The development of a SARS-CoV-2 infection reporting system facilitates the screening of compound libraries to discover new antiviral drugs. The study found that inhibitors of pyrimidine biosynthesis and NADPH oxidase (NOX) inhibitors have inhibitory effects on SARS-CoV-2 replication.
Article
Chemistry, Organic
Pierre Legrand, Yves L. Janin
Summary: This article reports an improved method for the synthesis of 2-hydroxypyrazines, which can enhance the regioselectivity and yield of the product. By using tetraalkylammonium hydroxide as the reaction parameter, starting from phenylglyoxal and alpha-aminoamides, pyrazine-containing new chemical entities of potential interest in medicinal chemistry were obtained.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yves L. Janin
Summary: This perspective paper discusses the challenges medicinal chemists face in drug discovery and emphasizes the importance of academic researchers in addressing these challenges. The paper presents successful examples of drug candidate discoveries and provides suggestions for contributions from academic medicinal chemists. It highlights the need for increased funding support for academic research in drug development.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Eloi P. Coutant, Sophie Goyard, Vincent Hervin, Glwadys Gagnot, Racha Baatallah, Yves Jacob, Thierry Rose, Yves L. Janin
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
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.
