Article
Chemistry, Multidisciplinary
Ziyan Zhang, Nikita Kvasovs, Anastasiia Dubrovina, Vladimir Gevorgyan
Summary: This method utilizes visible light-induced and Bronsted acid-assisted generation of hybrid palladium C(sp(3))-centered radical intermediate, enabling efficient transformation of a wide range of vinyl arenes, heteroarenes, and diazo compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Lenin Kumar Verdhi, Natalia Fridman, Alex M. Szpilman
Summary: A chiral nitroxide catalyst, generated in situ by a readily prepared chiral hydroxylamine precatalyst, in combination with a copper co-catalyst, serves as an environmentally friendly terminal oxidant for the enantioselective oxidative kinetic resolution of racemic axially chiral N-arylpyrrole alcohols, providing high enantioselectivity and reaction efficiency.
Article
Chemistry, Organic
Jiabin Shen, Jun Xu, Lei He, Yani Ouyang, Lin Huang, Wanmei Li, Qing Zhu, Pengfei Zhang
Summary: This study demonstrates a photoinduced rapid multicomponent cascade reaction of aryldiazonium salts with unactivated alkenes and trimethylsilyl azide under oxidant-free conditions, providing a synthetic route for a wide range of unsymmetric azo compounds. The compounds are obtained in good to excellent yields under mild reaction conditions. The control experiment confirms the reaction mechanism follows a radical pathway.
Article
Chemistry, Multidisciplinary
Yan Wang, Aying Yihuo, Lifeng Wang, Shunxi Dong, Xiaoming Feng
Summary: Asymmetric synthesis of enantioenriched azo compounds with tetrasubstituted stereocenter was achieved through chiral N,N'-dioxide/metal Lewis acid promoted interrupted Japp-Klingemann reaction. This protocol has a wide substrate scope and good functional group compatibility.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Bowen Li, Bangke Luo, He Yang, Wenjun Tang
Summary: This study reports an efficient palladium-catalyzed Heck reaction for the synthesis of heterocycles with α-heteroaryl substitution. The method exhibits a broad substrate scope and excellent functional group compatibility. The use of a sterically bulky ligand containing an anthryl moiety is crucial for this transformation. Additionally, an asymmetric variant of the Heck reaction has been achieved, enabling the efficient asymmetric synthesis of (S)-nicotine and its analogues via a cationic palladium pathway.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Kai-Lin Yin, Shuang Zhao, Ying Qin, Shu-Han Chen, Bo Li, Dongbing Zhao
Summary: A carbon-to-silicon switch is widely used in drug discovery. However, organosilicon compounds are not naturally occurring, so the development of effective synthetic methods is crucial for expanding their diversity. In this study, we have successfully synthesized a chiral bridged bicyclic silicon scaffold, which provides a new approach for the synthesis of chiral silicon compounds.
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, Multidisciplinary
Majid Mohammadnia, Nazanin Poormirzaei
Summary: A new magnetic nanocatalyst, Pd supported on 5-carboxyoxindole functionalized cell@Fe3O4 nanoparticles, was synthesized and successfully employed for the Heck-type arylation of different substituted maleimides. This green catalyst can be easily recovered and reused multiple times without significant loss of activity, providing a clean and efficient synthetic procedure.
NANOSCALE ADVANCES
(2021)
Article
Chemistry, Organic
Si Zhang, Ruo-Shi Jin, Yan-Fei Niu, Xing -Ping Zeng
Summary: A one-pot catalytic asymmetric approach to chiral quaternary-carbon-containing cyclobutanone-fused 4-aminoquinoline derivatives is presented. This process involves a chiral phosphoric acid-catalyzed desymmetric condensation of cyclobutane-1,3-diones with 2-halogenated anilines and a Pd-catalyzed coupling of the chiral enaminone intermediates with isocyanides. The reactions provide good to high yields and enantioselectivities, with up to 97% ee achieved.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Materials Science, Paper & Wood
Melike Caliskan, Talat Baran
Summary: A novel nanocatalyst system (Pd@CS-ZnO) was developed by attaching palladium nanoparticles onto a hybrid nanocomposite of chitosan and ZnO nanoparticles. The catalytic efficiency of Pd@CS-ZnO was assessed for Heck coupling reaction, showing promising results. The Pd@CS-ZnO nanocatalyst demonstrated easy separation and high chemical stability, making it a cost-effective and eco-friendly catalyst system.
Article
Chemistry, Multidisciplinary
Xiang Li, Gao-Wei Wang, Li-Xia Liu, Chang-Bin Yu, Yong-Gui Zhou
Summary: Here, the authors describe the first example of palladium-catalyzed asymmetric hydrogenolysis of easily accessible aryl triflates for the construction of axially chiral biaryl scaffolds. The resulting chiral biaryl compounds were used to prepare axially chiral monophosphine ligands, which were further employed in palladium-catalyzed asymmetric allylic alkylation with excellent enantioselectivities and high branched and linear ratios, highlighting the potential utility of this methodology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ting Wu, Qinghai Zhou, Wenjun Tang
Summary: The study presents a novel enantioselective alpha-carbonylative arylation reaction for the synthesis of chiral spiro beta, beta'-diketones with high yield and good to excellent enantioselectivities. Computational analysis suggests that the transformation proceeds through reductive elimination rather than nucleophilic addition pathway.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Sabrina Giofre, Letizia Molteni, Egle M. Beccalli
Summary: This Review presents the progress in catalytic enantioselective mono- and difunctionalization of alkenes, with a focus on the fundamental role of ligands. Various types of asymmetric reactions involving different bond formation, such as C-O, C-N, and C-C bonds, have been developed. The urgency to discover new ligands and synthetic methodologies is emphasized to enhance control over reaction selectivity and activity, and to expand the applications in the synthesis of heterocyclic scaffolds and biologically active compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Dilara Musaoglu, Hulya Avci Ozbek, Funda Demirhan
Summary: In this study, a new catalyst system was successfully developed for efficient coupling reactions of various aryl halides and olefins in Heck reactions. Catalytic studies demonstrated that using N,N'-bis(ferrocenylmethyl)imidazolinium chloride with a saturated imidazole ring as an auxiliary catalyst in the presence of Pd(OAc)(2) achieved high reaction efficiency in DMF solvent.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Applied
Ze-Jian Xue, Meng-Yao Li, Bin-Bin Zhu, Zhi-Tao He, Chen-Guo Feng, Guo-Qiang Lin
Summary: The palladium-catalyzed cross-coupling of ortho-vinyl aromatic bromides and olefins using a controllable 1,4-palladium migration/Heck cascade protocol is a mild, efficient, and highly stereoselective method for the synthesis of trisubstituted 1,3-dienes, especially triaryl-substituted ones.
ADVANCED SYNTHESIS & CATALYSIS
(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
Biochemical Research Methods
Izadora Fonseca Reis, Larissa Schumekel Foltran, Milena Helmer Lauer, Marcelo Henrique Gehlen, Roberta Lopes Drekener, Carlos Roque Duarte Correia
Summary: Two reactive phenanthrene derivatives were synthesized and used as fluorescent markers in fluorescence microscopy. These derivatives labeled silane modified Zeolite allowed good imaging resolution and spectroscopy measurements, with advantages in easy signal separation in confocal laser fluorescence microscopy. This also opens up the possibility of visualizing Zeolite-based materials commonly used as catalysts in thermal and photochemical reactions.
JOURNAL OF FLUORESCENCE
(2021)
Article
Chemistry, Medicinal
Michele Panciera, Emilio Lence, Angela Rodriguez, Begona A. Gracia, Jose Ainsa, Clara Marco-Marin, Vicente Rubio, Carlos Roque Duarte Correia, Concepcion Gonzalez-Bello
Summary: The therapeutic potential of 3H-pyrrolo[2,3-c]quinolines, the main core of Marinoquinoline natural products, has been explored for the development of new anti-TB agents. Two pyrroloquinolines (compounds 50 and 54) were discovered to have good in vitro activity against virulent strains of Mycobacterium tuberculosis. Enzymatic assays revealed that both compounds are inhibitors of glutamate-5-kinase (G5K), an essential enzyme for this pathogen.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Physical
Camila G. Vieira, Ricardo A. Angnes, Ataualpa A. C. Braga, Elena Gusevskaya, Liane M. Rossi
Summary: A smart catalytic oxidation route using Pd(OAc)2 and hydrogen peroxide in acetonitrile or acetone can produce (1R,5R)-sabinene, with distinct and pleasant smell suitable for fragrance and pharmacological applications. Three oxyfunctionalized products were obtained with ca. 80% combined selectivity, including two novel isomeric caranetype ketones with a bicyclo[4.1.0] skeleton. The findings support a proposed concerted mechanism for C-C activation, providing insights for future development of value-added products.
MOLECULAR CATALYSIS
(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
Shivashankar Kattela, Carlos Roque D. Correia, Abel Ros, Valentin Hornillos, Javier Iglesias-Sigu, Rosario Fernandez, Jose M. Lassaletta
Summary: A dynamic kinetic asymmetric Pd-catalyzed cross-coupling reaction of heterobiaryl bromides with ketone N-tosylhydrazones for the synthesis of heterobiaryl styrenes has been developed. The combination of Pd(dba)(2) as a precatalyst with a TADDOL-derived phosphoramidite ligand provides the corresponding coupling products with good yields and high enantioselectivities under mild conditions. Further reactions such as N-oxidation and N-alkylation of the products result in appealing functionalized axially chiral heterobiaryl derivatives.
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, 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
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, 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
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)
