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
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, Multidisciplinary
Caio C. Oliveira, Carlos Roque Duarte Correia
Summary: This article highlights the significance of the enantioselective palladium-catalyzed Heck-Matsuda reaction in the evolution of synthetic methods, as well as the interesting discoveries and synthetic opportunities that have emerged from our laboratory in this field.
Article
Chemistry, Applied
Tomaz Henrique Duarte Chorro, Edson Leonardo Scarpa de Souza, Otto Daolio Koster, Ellen Christine Polo, Rafaela Costa Carmona, Vitor Hugo Menezes da Silva, Joao Marcos Batista Junior, Carlos Roque Duarte Correia
Summary: A new enantioselective intramolecular strategy for the synthesis of enantioenriched bridged benzoxacines, unsaturated spirobenzofurans, 2,3-dihydrobenzofuran, and 2,3-indoline acetate scaffolds directly from anilines has been developed. The process combines in situ diazotization of the aniline with intramolecular Heck-Matsuda reaction, eliminating the need for isolation and purification of potentially unstable or hard-to-synthesize aryldiazonium salts. The method has been demonstrated to be practical and robust, achieving high yields and enantiomeric ratios.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Tao Zhang, Wen-Ao Li, Hong-Cheng Shen, Shu-Sen Chen, Zhi-Yong Han
Summary: An asymmetric Heck-Matsuda reaction targeting acyclic internal alkenes was successfully developed through the strategy of chiral anion phase transfer, resulting in high levels of enantioselectivity in the formation of chiral ketones. The use of a catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for suppressing palladium-hydride-mediated side reactions.
Article
Chemistry, Organic
Leanne M. Riley, Toni N. Mclay, Andrew Sutherland
Summary: Describes the synthesis and fluorescent properties of benzotriazole-derived alpha-amino acids that mimic L-tryptophan. Alkynyl-substituted analogues were prepared using nucleophilic aromatic substitution, benzotriazole formation via diazotization and cyclization, and a Sonogashira cross-coupling reaction. E-Alkenyl-substituted benzotriazoles were accessed by hydrogenation of alkynes. The alkynyl analogues showed higher quantum yields, stronger brightness, and solvatochromic sensitivity to polarity.
JOURNAL OF ORGANIC CHEMISTRY
(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, 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
Rifhat Bibi, Ismat Ullah Khan, Abbas Hassan
Summary: A structure selectivity relationship was established by modifying the ligand structure, which greatly influenced the catalytic activity and selectivity of the catalyst for non-activated substrates in the Heck-Matsuda reaction. The ligand 6MesPyoxsBu showed optimal catalytic activity and selectivity.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Ren-Xiao Liang, Jian-Fei Chen, Ying-Ying Huang, Ya-Ping Yu, Han-Yue Zhang, Yu-Feng Song, Gavin Chit Tsui, Yi-Xia Jia
Summary: Highly enantioselective palladium-catalyzed dearomative reductive Heck reaction and domino Heck-Suzuki reaction of 2-CF3-indoles have been developed. A variety of indolines bearing different stereocenters can be obtained using different reaction systems.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Zhiqiang Wei, Lixian Wen, Tixian Wen, Kaidi Zhu, Qian Wang, Yanchuan Zhao, Jinbo Hu
Summary: We report a new synthetic protocol for the selective perfluoro-tert-butylation of arenes. By using PFtB phenyl sulfone as a source of PFtB anion, highly regioselective reactions with arynes can yield perfluoro-tert-butylated arenes with high yields. The method is demonstrated by the preparation of sensitive 19F-labeled NMR probes with exceptional resolving ability.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Julien Berges, Yassir Zaid, Anis Tlili, Jean-Marc Sotiropoulos, Marc Taillefer
Summary: The Matsuda-Heck reaction, typically carried out with palladium catalysts, has been successfully done under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This study demonstrates a selective and direct synthesis of stilbenes from aryldiazonium salts at mild temperature, with mechanistic studies suggesting a radical pathway initiated by DMF.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
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, 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, Organic
Yurii Ostapiuk, Maksym Shehedyn, Oksana Barabash, Bohdan Demydchuk, Sviatoslav Batsyts, Colin Herzberger, Andreas Schmidt
Summary: Methyl 3-aryl-2-bromo-2-chloropropanoates were prepared via Meerwein reaction catalyzed by copper(II) bromide, and were utilized as starting materials for the synthesis of substituted 3-hydroxythiophenes. The structural variety of the obtained 2-substituted 5-aryl-3-hydroxythiophenes was achieved due to the wide range of available starting materials, including both anilines and thiols.
SYNTHESIS-STUTTGART
(2022)
Review
Chemistry, Multidisciplinary
Theodora W. Von Zuben, Daniel E. B. Moreira, Rafael L. Germscheidt, Rafael G. Yoshimura, Daniel S. Dorretto, Ana B. S. de Araujo, Airton G. Salles Jr, Juliano A. Bonacin
Summary: Hydrogen is a crucial molecule with various applications, especially in the fields of energy, transportation, and industry. It plays a significant role in decarbonization and sustainable development.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Carolina Gismene, Jorge Enrique Hernandez Gonzalez, Angela Rocio Nino Santisteban, Andrey Fabricio Ziem Nascimento, Lucas dos Santos Cunha, Fabio Rogerio de Moraes, Cristiano Luis Pinto de Oliveira, Caio C. Oliveira, Paola Jocelan Scarin Provazzi, Pedro Geraldo Pascutti, Raghuvir Krishnaswamy Arni, Ricardo Barros Mariutti
Summary: Staphylococcal exfoliative toxins (ETs), including the recently characterized ETE, are glutamyl endopeptidases that cleave a specific protein bond. The crystal structure of ETE revealed a unique structural feature and its existence of two conformations. Enzymatic assays showed no significant differences in activity between ETE and a mutant version, suggesting the structural feature may not impact enzyme activity. Additionally, ETE was found to form homodimers in solution, with monomerization being necessary for enzymatic activity.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Applied
Tomaz Henrique Duarte Chorro, Edson Leonardo Scarpa de Souza, Otto Daolio Koster, Ellen Christine Polo, Rafaela Costa Carmona, Vitor Hugo Menezes da Silva, Joao Marcos Batista Junior, Carlos Roque Duarte Correia
Summary: A new enantioselective intramolecular strategy for the synthesis of enantioenriched bridged benzoxacines, unsaturated spirobenzofurans, 2,3-dihydrobenzofuran, and 2,3-indoline acetate scaffolds directly from anilines has been developed. The process combines in situ diazotization of the aniline with intramolecular Heck-Matsuda reaction, eliminating the need for isolation and purification of potentially unstable or hard-to-synthesize aryldiazonium salts. The method has been demonstrated to be practical and robust, achieving high yields and enantiomeric ratios.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Carson Wiethan, Ingredy B. Braga, Vitor H. Menezes da Silva, Joao M. Batista Jr, Carlos Roque D. Correia
Summary: The enantioselective synthesis of isoindolones via Heck-Mizoroki reactions of endocyclic enamides using a palladium-bis(oxazoline) catalyst system is described. N,N-ligands prove to be an effective and low-cost alternative to phosphine-based chiral ligand counterparts. The intramolecular Heck reaction enables the construction of tricyclic isoindolones containing chiral centers in high yields and enantiomeric ratios.
Review
Chemistry, Organic
Edson Leonardo Scarpa de Souza, Caio C. C. Oliveira
Summary: This review discusses the use of aryldiazonium salts as a source of aryl radicals and their application in selective transformations over the past 13 years. Examples are categorized into thermal and photocatalytic transformations. It provides an accessible follow-up for both radical and catalytic chemists in industry and academia.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Analytical
Theodora Wrobel von Zuben, Cristiane Kalinke, Bruno Campos Janegitz, Airton Goncalves Salles Jr, Juliano Alves Bonacin
Summary: In this study, a non-enzymatic and metal-free ethanol sensor based on 3D PLA-graphene electrodes was developed. The sensor showed excellent performance in monitoring ethanol levels in saliva samples, meeting the legal limits for drivers in different countries. The 3D-printed sensor demonstrated high repeatability and reproducibility, making it a promising alternative approach for assessing ethanol levels in drivers while considering various legal regulations.
Article
Chemistry, Organic
Valdeir C. de Oliveira, Ricardo A. Angnes, Joao M. Batista Jr, Carlos Roque D. Correia
Summary: This work presents an effective method for the synthesis of chiral vinyl cyclopentenols via Heck desymmetrization of cyclopent-3-en-1-ylmethanol using vinyl triflates as coupling agents and chiral N,N ligands. The reaction exhibited high enantioselectivity and diastereoselectivity, with isolated yields of up to 80% and enantiomeric ratios of up to 97:3. The diastereoselectivities were rationalized through experiments using different vinyl triflates and the desymmetrization of a protected olefin substrate.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Analytical
Gabriela Freitas Pereira de Souza, Maria Fernanda Araujo Vieira Matos, Tharcilla de Castro Aglio, Airton Gonsalves Salles, Susanne Rath
Summary: In the last five years, the presence of N-nitrosamines in commonly used medicines has become a significant concern. A new method using bidimensional liquid chromatography-tandem mass spectrometry is proposed for quantifying N-nitrosamines in lipophilic active pharmaceutical ingredients (APIs), providing a way to monitor these compounds with low detection limits. The method has been validated and applied successfully for the quantification of N-nitrosamines in rifampicin.
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
(2023)
Article
Engineering, Environmental
Edson Leonardo Scarpa de Souza, Tomaz Henrique Duarte Chorro, Carlos Roque Duarte Correia
Summary: Arenediazonium salts are important aromatic organic compounds used as building blocks in academia and industry. Tetrafluoroborate arenediazonium salts are generally stable at room temperature, but those containing heteroatoms in the aromatic moiety can be problematic and unstable. This study evaluated the thermal stability and potential hazards of 58 common arenediazonium tetrafluoroborate salts, providing guidance for their safe use and handling in organic synthesis.
PROCESS SAFETY AND ENVIRONMENTAL PROTECTION
(2023)
Article
Chemistry, Organic
Gabriel S. G. Peagno, Airton G. G. Salles Jr
Summary: We propose a green and economically feasible approach for the photooxidation of various olefins using ammonium persulfate and blue light irradiation, which can result in the formation of vicinal diols from styrenes and aliphatic alkenes, and vinyl esters and diacids from alpha, beta-unsaturated ketones. The involvement of sulfate radicals has been established to be responsible for the selective production of the products. This method offers a significant advantage in terms of its wide substrate scope and economic feasibility, making it a promising alternative to conventional transition metal photocatalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Gilberto Duarte G. Ortin, Airton G. Salles Jr
Summary: This study describes a metal-free, persulfate-promoted route in water to access substituted biphenyl compounds. By employing biomass-derived compounds and phenylacetylenes, targeted products can be obtained with high yields and regioselectivity. This method contributes to the green synthesis initiative by utilizing renewable biomass-derived compounds in environmentally friendly methodologies.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lucas Scalon, Rodrigo Szostak, Francineide L. Araujo, Karla F. Adriani, Julian F. R. Silveira, Willian X. C. Oliveira, Juarez L. F. Da Silva, Caio C. Oliveira, Ana Flavia Nogueira
Summary: We report an improvement in efficiency and stability of perovskite solar cells after passivation with an organic molecule, decorated with two anilinium cations. The change in electron density distribution upon protonation and the presence of halide anion are key factors for the better passivation ability of the salt. Furthermore, the choice of counteranion significantly impacts device performance.
Article
Chemistry, Organic
A. A. Strekalova, A. A. Shesterkina, E. Shuvalova, C. R. D. Correia, Boqing Xu, Xuezhi Duan, Yanhui Yang, L. M. Kustov
Summary: The catalytic synthesis of isoprenol by hydrogenation of 3-methylbut-3-en-1-yl acetate on heterogeneous bimetallic Cu-Pt catalysts was successfully carried out for the first time. The best selectivity of isoprenol (76%) and full ester conversion were achieved using the 5%Cu-1%Pt/SiO2 catalyst within 6 hours.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guilherme Cariello Silva, Gabriela F. P. de Souza, Airton G. Salles
Summary: A redox-neutral C-H functionalisation in water using catalytic TEMPO to synthesize aminomethyl-substituted pyrroles is described. Starting from cheap and commercial chemical feedstocks (ketoesters and anilines), our method delivers targeted products in good yields and represents an effort to address redox economy in radical transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
A. Murashkina, A. D. Averin, S. P. Panchenko, A. S. Abel, O. A. Maloshitskaya, E. N. Savelyev, B. S. Orlinson, I. A. Novakov, C. R. D. Correia, I. P. Beletskaya
Summary: In this study, the N-arylation of n-octylamine and adamantane-containing amines with iodobenzene and its derivatives was achieved using copper(I) iodide and copper nanoparticles as catalysts in DMSO. Various ligands were used, and it was found that 2-isobutyrylcyclohexanone was the most efficient ligand. Higher yields of arylation products were obtained in the presence of copper nanoparticles, which could be recycled up to 9 times without significant loss of yield.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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)
