Article
Chemistry, Organic
Nastja Riemer, Martin Riemer, Mandy Krueger, Guy J. Clarkson, Michael Shipman, Bernd Schmidt
Summary: exo-Methylene-beta-lactams were synthesized in high yields as single isomers in a two-step reaction involving a Heck-type arylation with arene diazonium salts. The Pd-catalyzed coupling reaction showed high exo-regioselectivity and E-stereoselectivity in the beta-hydride elimination step. However, coupling products with aryl iodides, triflates, or bromides were obtained only in low yields due to extensive decomposition of the starting materials at elevated temperatures.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Ying Fu, Liang-Liang Guo, Xi Chen, Hao Chen, Jia-Jia Liu, Fang-Rong Li, Cai-Qin Xiao, Zhengyin Du
Summary: A Cu/Pd co-catalyzed Catellani-type ortho arylation reaction of iodoarenes with aryl diazonium salts has been developed. Aryl radicals that derived from aryl diazonium salts were regioselectively installed at ortho position of iodoarenes via palladium catalyzed C-H activation. Mechanistic studies showed that, in contrast to classical Pd0-PdII-PdIV-PdII-Pd0 catalytic cycle, this radical cascades performed via a Pd0-PdII-PdIII-PdI-Pd0 cycle.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Andreas Krause, Eric Sperlich, Bernd Schmidt
Summary: Itaconic acid esters and hemiesters undergo efficient Pd-catalyzed coupling reactions with arene diazonium salts, leading to the synthesis of benzazepine-2-ones in one to two steps with high yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xianfeng Li, Juan Zhang, Changyang Liu, Jie Sun, Yangfeng Li, Gong Zhang, Yizhou Li
Summary: This article reports on a palladium-catalyzed cross-coupling technique using DNA-conjugated aryl diazonium intermediates for DNA-encoded chemical library synthesis. The method allows for the synthesis of diverse chemical compounds with broad substrate scope and excellent functional group tolerance under mild conditions. It also enables the construction of DNA-tethered pharmaceutical compounds without compromising their bioactivity. This approach demonstrates its potential for creating medicinally relevant combinatorial libraries and investigating protein-ligand interactions in pharmaceutical research.
Article
Chemistry, Organic
Rochelle McGrory, Rebecca Clarke, Olivia Marshall, Andrew Sutherland
Summary: The Heck-Matsuda coupling reaction of arenediazonium salts derived from l-phenylalanine with various alkenes has been developed, enabling the synthesis of unnatural α-amino acids with cinnamate, vinylsulfone, and stilbene side-chains. The photophysical analysis shows that the (E)-stilbene analogues exhibit enhanced fluorescence properties compared to l-phenylalanine, with red-shifted absorption and emission spectra and larger quantum yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Italo A. Sanhueza, Felix J. R. Klauck, Erdem Senol, Sinead T. Keaveney, Theresa Sperger, Franziska Schoenebeck
Summary: The study found that aryl diazonium salts exhibit different reactivities in Suzuki and Stille cross-couplings in MeOH, challenging the currently accepted mechanism. Experimental evidence suggests that the observed solvent dichotomy is primarily due to the formation of unreactive Pd(II)-methoxy intermediates with arylstannanes, but highly reactive with arylboronic acids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Christian Leonardo Herrera, Joao Victor Santiago, Julio Cezar Pastre, Carlos Roque Duarte Correia
Summary: This study describes a method for the enantioselective Heck-Matsuda reaction of cyclic and acyclic olefins directly from anilines. The method demonstrates a broad substrate scope and high enantioselectivity and yield in the synthesis of Heck adducts.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Cooper A. Vincent, Alexia Ripak, Ludovic Troian-Gautier, Uttam K. Tambar
Summary: A photocatalytic method is presented for converting aryl diazonium salts to aryl sulfonyl fluorides, which have emerged as powerful tools for selective protein labelling in chemical biology. The diazonium substrates can be easily obtained from functionalized anilines in one step. The optimization of this mild synthesis method for sulfonyl fluorides, as well as the range of conversion with functionalized diazonium salts, is discussed along with photophysical measurements providing detailed information on the mechanism of the photochemical process. © 2023 Elsevier Ltd. All rights reserved.
Article
Chemistry, Medicinal
Jailton de Souza-Ferrari, Edvaldo Alves Silva-Junior, Juliana Alves Vale, Luise Araujo de Albuquerque Simoes, Manoel Oliveira de Moraes-Junior, Bruna Braga Dantas, Demetrius Antonio Machado de Araujo
Summary: This study demonstrated a late-stage diversification of unactivated olefins through Heck-Matsuda arylation to synthesize a series of novel aryl-labdane-type derivatives, showing significant cytotoxic activity against cancer cell lines, with one compound exhibiting selective effects. Further biological investigations suggested that the observed cytotoxic activity might be mediated by cell cycle arrest and autophagy-induced cell death, indicating potential for anticancer activity against chronic myeloid leukemia from aryl-labdane-type derivatives.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Wei Sun, Luke Wilding-Steele, Richard C. D. Brown, David C. C. Harrowven
Summary: Benzyloxy iodobenzene ethers can undergo cyclisation to form benzo[c]chromenes under UVC irradiation without the need for reagents or catalysts. The reactions proceed through the generation of triplet aryl cations, 5-exo and 3-exo-cyclisations, and subsequent rearomatisation. This methodology is versatile, convenient, and applicable to various related ring systems.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Multidisciplinary
Jianli Chen, Xiaoxuan Xie, Jiming Liu, Zhiqun Yu, Weike Su
Summary: Aryl diazonium salts are important in chemical transformations, but their explosive nature restricts their use in batch reactions. Continuous flow technology provides a safer and more efficient way to utilize diazotization and aryl diazonium salts, improving reaction efficiency and industrial potential. However, the transition from batch to continuous flow also presents new challenges.
REACTION CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Dilip V. Patil, Karu Ramesh, Hun Young Kim, Kyungsoo Oh
Summary: The visible light excitation of areneazo-2-(2-nitro)-propane center dot HCl salts generated singlet aryl cation that underwent aromatic S(N)1 reactions with various nucleophiles. The stabilization of the in situ generated singlet aryl cation by a counter nitronate anion prevented other intersystem crossing and single electron transfer processes. With improved safety features, the current visible light-promoted reactions provide an alternative strategy for aryl C-sp(2)-X bond formation.
Article
Chemistry, Organic
Swantje Lerch, Stefan Fritsch, Thomas Strassner
Summary: This study reports the use of TAAILs as solvents in the Mizoroki-Heck reaction. By optimizing the reaction conditions, efficient synthesis of (E)-stilbene derivatives with high yields was achieved. The catalytic system using TAAILs showed higher yields compared to other commercially available ionic liquids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Huan Chen, Philippe Nizard, Philippe Decorse, Sophie Nowak, Souad Ammar-Merah, Jean Pinson, Florence Gazeau, Claire Mangeney, Yun Luo
Summary: The design of dual-mode fluorescence and Raman tags has aroused great interest in biomedical imaging and sensing. In this study, lanthanide-doped fluoride nanoparticles were functionalized with Raman tags using aryl diazonium salt chemistry, and successfully used as bimodal fluorescent-Raman probes for cell bioimaging. This new generation of nanoprobes offers unprecedented opportunities for biomedical applications.
Review
Chemistry, Organic
Xin Zhang, Yaoyao Mei, Yangyang Li, Jingang Hu, Dayun Huang, Yicheng Bi
Summary: This review discusses the advances of aryl diazonium salts in light-mediated reactions, categorizing them into five groups based on the types of bond formations. Various reactions such as radical addition, metal-catalyzed coupling, and C-H activation are discussed in this context.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Vincent Fernandez, Daniyal Kiani, Neal Fairley, Francois-Xavier Felpin, Jonas Baltrusaitis
APPLIED SURFACE SCIENCE
(2020)
Article
Chemistry, Applied
Ehu Camille Aka, Eric Wimmer, Elvina Barre, Daniel Cortes-Borda, Tchirioua Ekou, Lynda Ekou, Mireia Rodriguez-Zubiri, Francois-Xavier Felpin
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Applied
Florian Carpentier, Francois-Xavier Felpin, Francoise Zammattio, Erwan Le Grognec
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Physical
Shrikant Kunjir, Mireia Rodriguez-Zubiri, Vincent Coeffard, Francois-Xavier Felpin, Patrick Giraudeau, Jonathan Farjon
Article
Chemistry, Applied
N. Vasudevan, Eric Wimmer, Elvina Barre, Daniel Cortes-Borda, Mireia Rodriguez-Zubiri, Francois-Xavier Felpin
Summary: This article presents a continuous-flow strategy for the palladium-catalyzed direct C-H arylation of indole-3-acetic acid derivatives with arenediazonium salts, optimizing the coupling reaction in a three-dimensional space using a fully autonomous self-optimizing flow platform. The developed flow methodology is experimentally simple, mild, broad in scope, and safer than traditional batch approaches, particularly suitable for preparing precursors of pharmaceutically relevant compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Materials Science, Multidisciplinary
Marie Denis, Denis Gindre, Francois-Xavier Felpin
Summary: Cyclopropenone derivatives are used as latent photo-released strained cyclic alkynes for covalent printing complex patterns on cellulose paper. The use of a simple UV LED allows quick printing at room temperature with good resolution at the micrometer scale and minimal diffusion. The strategy is proven effective through the sequential printing of a QR code and logo on the same paper sheet.
JOURNAL OF MATERIALS SCIENCE
(2021)
Article
Chemistry, Organic
Aline Makhloutah, Danylo Hatych, Thomas Chartier, Lou Rocard, Antoine Goujon, Francois-Xavier Felpin, Pietrick Hudhomme
Summary: An unprecedented palladium-catalyzed cross-coupling reaction has been reported, allowing for the grafting of aryls in the bay region of PDIs with high selectivity. This reaction has been optimized and successfully applied for the desymmetrization of dinitro-PDI substrates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Bi Bali Judicael Tra, Abolle Abolle, Vincent Coeffard, Francois-Xavier Felpin
Summary: This paper presents a divergent continuous-flow approach for the biomimetic oxidative cyclization of reticuline-type alkaloids to aporphine and morphinandienone natural products using hypervalent iodine(III) reagents. The method allows for the selective synthesis of target products based on detailed knowledge of the reaction mechanisms, providing robust conditions for the preparation of natural products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Applied
Mireia Rodriguez-Zubiri, Francois-Xavier Felpin
Summary: The concept and practices of chemical synthesis are transforming towards fully autonomous continuous processes, which require efficient monitoring and online analysis. This review presents the main in-line/online analytical tools for monitoring chemical reactions, serving as a guide for synthetic chemists.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Multidisciplinary
Kouakou Eric Konan, Abolle Abolle, Elvina Barre, Ehu Camille Aka, Vincent Coeffard, Francois-Xavier Felpin
Summary: Continuous flow photo-thiol-ene reactions on cinchona alkaloids with a variety of organic thiols have been developed to deliver a series of unprecedented architectures. A self-optimizing flow photochemical reactor was used to identify the optimal experimental conditions. The flow thiol-ene reaction proceeds under mild conditions, maximizing photon absorption and increasing reaction rates and yields compared to traditional batch reactors.
REACTION CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
N. Vasudevan, Ehu C. Aka, Elvina Barre, Eric Wimmer, Daniel Cortes-Borda, Patrick Giraudeau, Jonathan Farjon, Mireia Rodriguez-Zubiri, Francois-Xavier Felpin
Summary: This study presents a straightforward continuous flow synthesis of FGIN-1-27, a compound with potent anxiolytic effects, from inexpensive and commercially available starting materials. The four-step synthesis includes the direct C-H arylation of an indole with an arenediazonium salt. The use of enabling technologies such as real-time in-line benchtop F-19 NMR analysis and an optimization algorithm improves process safety and reduces the number of experiments needed in optimization campaigns.
REACTION CHEMISTRY & ENGINEERING
(2021)
Meeting Abstract
Gastroenterology & Hepatology
Adeline Sivignon, Antoine Chaprenet, Francois-Xavier Felpin, Julie Bouckaert, Sebastien G. Gouin, Nicolas Barnich
Article
Chemistry, Multidisciplinary
Eric Wimmer, Daniel Cortes-Borda, Solene Brochard, Elvina Barre, Charlotte Truchet, Francois-Xavier Felpin
REACTION CHEMISTRY & ENGINEERING
(2019)
Article
Chemistry, Multidisciplinary
Madeleine Cauwel, Adeline Sivignon, Clarisse Bridot, Medy C. Nongbe, David Deniaud, Benoit Roubinet, Ludovic Landemarre, Francois-Xavier Felpin, Julie Bouckaert, Nicolas Barnich, Sebastien G. Gouin
CHEMICAL COMMUNICATIONS
(2019)
Article
Materials Science, Multidisciplinary
Guillaume Bretel, Erwan Le Grognec, Denis Jacquemin, Takashi Hirose, Kenji Matsuda, Francois-Xavier Felpin
ACS APPLIED POLYMER MATERIALS
(2019)
