Article
Chemistry, Multidisciplinary
Argha Saha, Srimanta Guin, Wajid Ali, Trisha Bhattacharya, Sheuli Sasmal, Nupur Goswami, Gaurav Prakash, Soumya Kumar Sinha, Hediyala B. Chandrashekar, Sanjib Panda, S. S. Anjana, Debabrata Maiti
Summary: The Fujiwara-Moritani reaction has made a significant contribution to contemporary C-H activation protocols. By establishing a photoredox catalytic system, the regioselective Fujiwara-Moritani reaction can be achieved through visible light without the need for silver salts and thermal energy. This sustainable protocol has importance in synthesizing natural products, chiral molecules, drugs, and diversifying functionalizations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(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
Multidisciplinary Sciences
Dingyi Wang, Xiangyang Chen, Jonathan J. Wong, Liqun Jin, Mingjie Li, Yue Zhao, K. N. Houk, Zhuangzhi Shi
Summary: This study presents a regioselective C7-H silylation of indole derivatives assisted by strong coordination of the palladium catalyst with a phosphorus directing group. The method allows for the effective synthesis of various C7-silylated indoles with broad functional group compatibility. Additionally, the hypothesis regarding the P(III)-directed C-H metalation event is successfully tested through mechanistic experiments and DFT calculations.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Takahiro Doba, Laurean Ilies, Wataru Sato, Rui Shang, Eiichi Nakamura
Summary: The study discovered that diethyl oxalate, in combination with AlMe3, acts as a two-electron acceptor in iron-catalysed C-H activation, enabling regioselective thienyl C-H/C-H coupling. Ligand optimization accelerated the polymerization of thiophene-containing monomers, resulting in polymers with various electron-donative pi motifs. This highlights the versatile potential of iron catalysis for the synthesis of functional polymers.
Article
Chemistry, Multidisciplinary
Wei Tian, Bowen Li, Duanshuai Tian, Wenjun Tang
Summary: A palladium-catalyzed 2-alkylation of indoles with alpha-bromo esters using a P,P=O ligand has been developed. The method shows excellent regioselectivities, mild reaction conditions, and good functional group compatibility. Mechanistic studies indicate that the reaction proceeds through a radical pathway.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Jingqiang Han, Huimin Yu, Weiwei Zi
Summary: This study reported a regioselective hydroarylation reaction of unactivated alkenes with aryl boronic acids directed by carboxylic acid. The reaction was achieved by using a homogeneous manganese catalyst MnBr(CO)(5) in the presence of KOH and H2O in the m-xylene reaction medium. Both internal and terminal alkenes showed good reactivity in this transformation, and a variety of functional groups were tolerated.
Article
Chemistry, Organic
Ignacio Medina-Mercado Susana Porcel
Summary: A gold-catalysed coupling reaction between aryldiazonium salts and arylboronic acids is described. The reaction proceeds efficiently under blue LED irradiation in the presence of KF and a catalytic amount of ascorbic acid, yielding satisfactory results. Notably, 4-nitrobenzendiazonium tetrafluoroborate exhibits sufficient reactivity to undergo the coupling reaction with various arylboronic acids even in the absence of aryl radical initiators. This coupling reaction is applicable for substrates with electron-donating and electron-withdrawing groups at the para, ortho, and meta positions.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Applied
Yuki Kanai, Dorian Mueller-Borges, Herbert Plenio
Summary: The direct arylation of 1,3-benzodioxole and 2,2-difluorobenzo[1,3]dioxole with various aryl bromides yields 4-substituted products in high yields. The nature of the amide and the concentration of the reactants play crucial roles in optimizing reaction conditions. Acetamide acts as a ligand to Pd, not as a solvent, in this reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Ran Ding, Yu-Hang Deng, Shan Luo, Xue-Feng Tang, Lei Liu, Pei-Long Wang
Summary: This article describes a regioselective cascade cyclization method using vinyl-tethered alkynes to construct 1,2-dihydropyridines. The method has good functional group compatibility, mild conditions, and provides an environmentally friendly approach.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Zhucheng Zhang, Qian He, Xiaofei Zhang, Chunhao Yang
Summary: A method of direct C-4 selective alkylation of pyridines under visible light irradiation at room temperature is reported. The method uses simple maleate-derived pyridinium salts as pyridine precursors and readily available carboxylic acid-derived N-(acyloxy)phthalimides as alkyl radical precursors, affording good to excellent yields without using stoichiometric oxidants and acids.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Qiang Wang, Shuaijie Wu, Yi-Dong Wang, Jing Sun, Ying Han, Chao-Guo Yan, Lei Wang
Summary: Here, a new and efficient strategy for the synthesis of alkenyl sulfoxides is reported. The method involves the transition metal-free C-S cross-coupling reaction between sulfenate anions and alkenylsulfonium salts. The in situ generation of sulfenate anions from beta-sulfinyl esters under mild conditions provides an effective approach for the synthesis of diverse alkenyl sulfoxides in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Rajeev V. Hegde, Tiow-Gan Ong, Ram Ambre, Arvind H. Jadhav, Siddappa A. Patil, Ramesh B. Dateer
Summary: This study achieved regioselective C2 arylation of indoles, benzothiophene, and benzofuran without directing group using affordable Pd NPs and NHC-Pd@MNPs catalyst. The reusable catalyst efficiently produced C2 arylated heterocycles in good to excellent yield, with potential for gram-scale synthesis. The reaction mechanism was supported by control experiments and literature precedents.
Article
Chemistry, Organic
Hong Qin, Jie Zhang, Kai Qiao, Dong Zhang, Wei He, Chengkou Liu, Zheng Fang, Kai Guo
Summary: A highly regioselective and atom-efficient strategy for the construction of fused free (NH) heteroarenes through a palladium-catalyzed perfluoroalkyl insertion reaction has been developed. This method utilized multiple iodofluoroalkanes as practical perfluoroalkyl sources, providing a simple and versatile route for the synthesis of perfluoroalkylated indoles. Furthermore, it was also applied to late-stage C2 perfluoroalkylation of bioactive compounds such as auxin, tryptophan, and melatonin analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kuan Liu, Dexiang Ding, Weitao Xing, Long Liu, Shuo Zhang, Qi Meng, Tieqiao Chen
Summary: A palladium-catalysed carbon-carbon bond-forming reaction using organoammonium salts and carboxylic acids was developed. Various carboxylic acids, including polyfluoroaromatic carboxylic acids, propiolic acids, and alpha-cyano benzyl carboxylic acid, reacted smoothly with benzyl ammonium salts to give the desired coupling products in good-to-excellent yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Devesh Chandra, Nikunj Kumar, Sumit, Diksha Parmar, Puneet Gupta, Upendra Sharma
Summary: A regioselective C8 linear olefination of isoquinoline-1H-2-one with terminal (aromatic and aliphatic) alkynes is reported under Co(iii) catalysis. This study is the first to demonstrate the C8 functionalization of isoquinolone using non-noble transition metal complexes. Experimental and computational mechanistic studies have been conducted to elucidate the reaction pathway.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Physical
Jaqueline F. de Souza, Matheus S. Gularte, Rafael F. N. Quadrado, Andre F. P. Biajoli, Andre R. Fajardo
Summary: This paper comprehensively discusses the development and application of catalysts based on Cu-supported in polysaccharide-based materials. Polysaccharides have attractive characteristics that enable the development of support materials with varied sizes and geometry capable of immobilizing various Cu species.
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING
(2023)
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)
Review
Chemistry, Organic
Rafael Dias do Espirito Santo, Rebeca Monique Capitao, Patricia Santos Barbosa, Eric Francisco Simao dos Santos, Carlos Roque Duarte Correia
Summary: In recent years, the heterocyclic 3H-pyrrolo[2,3-c]quinoline system and its closely related natural products, the marinoquinolines, have garnered significant attention for their intriguing chemistry and diverse biological activities. The marinoquinolines exhibit various biological activities, such as antiplasmodial, antibacterial, and antifungal properties, which have driven the development of new strategies to obtain natural products and derivatives.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Jaqueline F. de Souza, Thalia S. A. Lemos, Andre F. P. Biajoli, Andre R. Fajardo
Summary: In this study, we investigated the activation and stabilization of Pd nanoparticles using chitosan microparticles functionalized with phosphine moieties. The catalytic activity of the prepared material was evaluated in Heck reactions, showing promising results in terms of yields and reaction scope. Comparative experiments confirmed the superiority of the phosphine-modified material compared to a similar catalyst derived from non-functionalized chitosan. Furthermore, the prepared catalyst exhibited considerable activity even after four consecutive reaction runs, with minimal Pd leaching.
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
Plant Sciences
Catarina G. Pereira, Carolina Borsoi Moraes, Caio H. Franco, Clarissa Feltrin, Raphael Grougnet, Euzebio Guimaraes Barbosa, Michele Panciera, Carlos Roque D. Correia, Maria Joao Rodrigues, Luisa Custodio
Summary: Marine halophytes are a valuable source of natural products with potential anti-infectious properties, among which sea fennel flower decoction showed significant anti-Trypanosoma cruzi activity. This suggests sea fennel as a promising candidate for the treatment of Chagas disease.
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
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.
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, 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)
