Article
Chemistry, Multidisciplinary
Vincent M. Kassel, Christopher M. Hanneman, Connor P. Delaney, Scott E. Denmark
Summary: Reaction conditions have been developed for refractory heteroaryl-heteroaryl Suzuki-Miyaura cross-couplings using neopentyl heteroarylboronic esters, heteroaryl bromides and chlorides, and potassium trimethylsilanolate (TMSOK) under anhydrous conditions. The addition of trimethyl borate enhances reaction rates by several mechanisms, enabling cross-coupling of diverse reaction partners in good yields and short reaction times.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Trong Nguyen Huu Phan, Jihong Lee, Hyunik Shin, Jeong-Hun Sohn
Summary: The Pd-catalyzed/Cu-mediated oxidative dehydrosulfurative carbon-oxygen cross-coupling reaction offers a facile access to biologically and pharmacologically valuable 2-aryloxypyrimidine derivatives due to the ready availability of diverse DHPMs and aryl alcohols.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Qi Wang, Zhongxia Shang, Haiyan Wang, Alexander Wei
Summary: Colloidal Ag particles decorated with Fe3O4 islands can be activated as inverse catalysts for C(sp(2))-H heteroarylation either electrochemically or photochemically. The silver-iron oxide (SIO) particles are reduced into redox-active forms by cathodic charging at mild potentials or short-term light exposure, and can be reused multiple times by magnetic cycling without further activation. The reduction peak shift is attributed to the overpotential produced by surface Fe3O4, which separates residual Ag ions or clusters from bulk silver. The catalytic efficiency of SIO is maintained even with acid degradation, and can be counteracted by simple addition of water to the reaction medium.
Article
Chemistry, Applied
Sara Payamifar, Foad Kazemi, Babak Kaboudin
Summary: This study introduced a convenient nickel-catalyzed protocol for the Suzuki-Miyaura coupling reaction using a simple mixture of Ni(II) and unfunctionalized beta-cyclodextrin in water. The environmentally friendly and cost-efficient method allows the synthesis of biaryls from arylboronic acids and various aryl halides. The catalyst can be recycled for multiple runs with only a small decrease in catalytic activity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Guangwu Sun, Herui Liu, Xiu Wang, Wenbo Zhang, Wenjun Miao, Qinyu Luo, Bing Gao, Jinbo Hu
Summary: In this manuscript, a novel palladium-catalyzed coupling reaction between gem-difluoroalkenes and aryl boronic acids is reported, which yields bioactive indane-type ketones with an all-carbon alpha-quaternary center. The mechanism involves a water-induced defluorination and cross-coupling cascade pathway, supported by characterization and stoichiometric reactions of the key intermediates RCF2PdII. The use of vinyl difluoromethylene motif as an in situ carbonyl precursor is unprecedented in transition-metal-catalyzed coupling reactions, and it is expected to spark broad interest in ketone synthesis, fluoroalkene functionalization, and design of new synthetic protocols based on the unique reactivity of difluoroalkyl palladium(II) species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Ruizhe Wang, Xinyu Wang, Shuai Mao, Yahao Zhao, Bo Yuan, Xue-Yan Yang, Jianjun Li, Zhengkai Chen
Summary: A light-mediated C-Se bond coupling reaction between aryl halides and diselenides has been achieved under mild and photocatalyst-free conditions, resulting in the synthesis of aryl selenoethers. The transformation offers readily available materials, mild reaction conditions, a broad substrate scope, and high efficiency. A plausible mechanism has been proposed based on the initial mechanistic investigation, and the protocol is also applicable for forging C-S and C-Te bonds using disulfides and ditellurides.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Dejiang Zhang, Zhi Xu, Ting Tang, Liyuan Le, Cairong Wang, Nobuaki Kambe, Renhua Qiu
Summary: In this study, a general method for the synthesis of unsymmetric diarylmethanes from (hetero)aryl methylhalides and Sb-aryl stibines is described. The protocol has a broad substrate scope and good functional group tolerance. Gram-scale synthesis of drug molecules and their derivatives was efficiently achieved using this method.
Review
Chemistry, Multidisciplinary
Shelesh Krishna Saraswat, Ramanjaneyulu Seemaladinne, Media Noori Abdullah, Halim Zaini, Nabeel Ahmad, Nafis Ahmad, Esmail Vessally
Summary: Aryl fluorosulfates are versatile building blocks in organic synthesis and have gained increasing attention in SuFEx click chemistry. They can be easily prepared from phenols using low-cost sulfuryl fluoride as a sulfonyl fluoride provider. They have been used as less toxic and more atom economical alternatives to triflates in numerous cross-coupling reactions. This review summarizes the recent advances and developments in utilizing aryl fluorosulfates as electrophilic partners in cross-coupling reactions.
Article
Chemistry, Organic
Chen Zhang, Na-Na Ma, Zi-Lun Yu, Chuanji Shen, Xiaocong Zhou, Xue-Qiang Chu, Weidong Rao, Zhi-Liang Shen
Summary: The efficient palladium-catalyzed direct reductive cross-coupling reaction proceeds smoothly at room temperature with moderate to good yields, showing reasonable functional group tolerance. The one-pot reaction using readily available aryl bromide as a coupling partner is simple to handle, avoiding the use of pre-prepared organometallic reagents.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Jiajia Li, Junmin Chen, Hefeng Zhu, Mingzhong Cai
Summary: A new mesoporous SBA-15-anchored triphenylphosphine-gold(i) complex [SBA-15-Ph(3)PauNTf(2)] was synthesized and characterized. This catalyst allowed for the photosensitizer-free cross-coupling reaction of aryldiazonium tetrafluoroborates and alkynyltrimethylsilanes under blue LED irradiation, yielding diverse arylalkynes with good yields and high functional group tolerance. The catalyst could be easily recovered and reused multiple times without significant loss in activity.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaoshen Ma, Charles S. Yeung
Summary: Our study focused on achieving C(sp(2))-C(sp(3)) coupling reactions using 2,2-difluorobicyclo[1.1.1]pentane (BCP-F-2) building blocks. Through comparison of reactivities between BCP and BCP-F-2 analogues, we found that the Barluenga coupling reaction showed promising results, expanding the potential applications of BCP-F-2 in organic chemistry and medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Xinyu Guan, Haoran Zhu, Tom G. Driver
Summary: A simple copper-catalyzed reaction involving nitroarenes and aryl boronic acids to form diarylamines has been described, with phenyl silane as the stoichiometric terminal reductant. The cross-coupling reaction requires low concentrations of CuX and diphosphine, tolerates a wide range of functional groups, and proceeds via a nitrosoarene intermediate catalyzed by copper.
Article
Chemistry, Organic
Shan Jiang, Zi-Tong Zhang, David James Young, Lu-Lu Chai, Qi Wu, Hong-Xi Li
Summary: A photoinduced nickel-catalyzed cross-coupling reaction of arylsulfinates with (hetero)aryl halides has been achieved using visible light. The reaction showed a broad substrate scope and good functional group tolerance, providing diarylsulfones in moderate to excellent yields. The mechanism involves oxidative addition, single-electron oxidation, reductive elimination, and electron transfer.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Shan Jiang, Zi-Tong Zhang, David James Young, Lu-Lu Chai, Qi Wu, Hong-Xi Li
Summary: In this study, a photoinduced nickel-catalyzed cross-coupling reaction was achieved with moderate to excellent yields of arylsulfinates and (hetero)aryl halides. The reaction demonstrated a broad substrate scope and good functional group tolerance, leading to the formation of diarylsulfones. The mechanism involved several steps, including oxidative addition, oxidation, reductive elimination, and release of the product. The photoredox and nickel catalytic cycles interacted through electron transfer.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Pan Pan, Shihan Liu, Yu Lan, Huiying Zeng, Chao-Jun Li
Summary: A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. Hydrazones were used as alternatives to organometallic reagents, making this cross-coupling mild and green. Mechanistic investigations revealed the formation of an electron donor-acceptor complex, generating an aryl radical via single-electron transfer.
Review
Biochemistry & Molecular Biology
Flavio A. R. Barbosa, Romulo F. S. Canto, Kerolain F. Teixeira, Anacleto S. de Souza, Aldo S. de Oliveira, Antonio L. Braga
Summary: Alzheimer's disease (AD) is a prevalent type of dementia that affects millions of older people worldwide. Selenium-containing compounds have shown potential as multi-targeted drugs for the treatment of AD due to their antioxidant and anticholinesterase properties. These compounds can decrease the aggregation of amyloid-beta (A beta), a key feature of AD. Some selenium-derived compounds have molecular features similar to FDA-approved drugs, suggesting that they may have optimized pharmacokinetic properties.
CURRENT MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Joelma M. M. Sarturi, Luciano Dornelles, Natalia V. V. Segatto, Tiago Collares, Fabiana K. K. Seixas, Bruna Candia Piccoli, Fernanda D'Avila da Silva, Folorunsho Bright Omage, Joao Batista Teixeira da Rocha, Renata A. A. Balaguez, Diego Alves, Eder J. J. Lenardao, Eric F. F. Lopes, Anna Kula-Pacurar, Krzysztof Pyrc, Luca Sancineto, Oscar E. D. Rodrigues
Summary: This study synthesized and evaluated the multi-target behavior of new 5'-hydroxy-3-(chalcogenyl-triazoyl)-thymidine derivatives as antioxidant and anti-HIV agents. The compounds showed good activity and no apparent toxicity in mice. The design strategy of modifying the AZT nucleus via the 1,3-dipolar Huisgen cycloaddition reaction proved effective in achieving the desired biological activities.
CURRENT MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kimberly Benedetti Vega, Jose Antonio Campos Delgado, Lucas V. B. L. Pugnal, Burkhard Koenig, Jose Tiago Menezes Correia, Marcio Weber Paixao
Summary: In this study, a strategy for the precise installation of sulfones and carboxylic acids onto styrenes using sodium sulfinates and CO2 as coupling partners was described. The protocol allowed for the preparation of carboxy-sulfonylated compounds with high yields and broad functional group tolerance. Additionally, a one-pot photocatalytic carboxy-sulfonylation-elimination strategy was developed for the synthesis of alpha-aryl-acrylates by taking advantage of the leaving group ability of the sulfone moiety.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Neurosciences
Mikaela Peglow Pinz, Renata Leivas de Oliveira, Caren Aline Ramson da Fonseca, Guilherme Teixeira Voss, Beatriz Pereira da Silva, Luis Fernando Barbosa Duarte, William Borges Domingues, Hadassa Gabriela Ortiz, Anne Suely Pinto Savall, Flavia Carla Meotti, Diego Alves, Vinicius Farias Campos, Simone Pinton, Ethel Antunes Wilhelm, Cristiane Luchese
Summary: In this study, the researchers found that treatment with FSP can alleviate memory impairment and sensitivity to pain caused by Aβ, by exerting its effects against oxidative stress and neuroinflammation.
MOLECULAR NEUROBIOLOGY
(2023)
Article
Neurosciences
Mariana G. Fronza, Manoela Sacramento, Diego Alves, Domenico Pratico, Lucielli Savegnago
Summary: This study demonstrates that QTC-4-MeOBnE has a moderate effect in a transgenic model of AD, preventing memory impairment and depressive-like behavior, and modulating multiple pathways involved in the onset and progression of AD.
MOLECULAR NEUROBIOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Marcelo Heinemann Presa, Marcia Juciele da Rocha, Camila Simoes Pires, Kauane Nayara Bahr Ledebuhr, Gabriel Pereira da Costa, Diego Alves, Cristiani Folharini Bortolatto, Ceisar Augusto Bruning
Summary: This study evaluated the antidepressant-like effect of a hybrid compound containing triazole and acetophenone, demonstrating that it modulates the serotonergic system through 5-HT2A/2C and 5-HT4 receptors and inhibits monoamine oxidase A activity in the hippocampus. The compound showed penetration into the central nervous system and low toxicity at a high dose, making it an interesting candidate for the development of a new therapeutic strategy for major depressive disorder (MDD).
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Chemistry, Organic
Gabriel P. P. Da Costa, Gustavo B. B. Blodorn, Thiago Barcellos, Marcio S. Silva, Rafael Luque, Diego Alves
Summary: We described a simple and metal-free protocol for the synthesis of [1,2,3]triazolo[1,5-a]quinoline 3-carboxamides. The synthesis involves two steps, with the first step utilizing organocatalysis and the second step involving the use of an inorganic base. The reactions were performed in dimethylsulfoxide as solvent at 70°C for 2 hours. The synthetic protocol yielded a variety of [1,2,3]triazolo[1,5-a]quinoline 3-carboxamides in good to excellent yields (63-96%) for secondary compounds and moderate to good yields (48-76%) for tertiary compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Tais da Silva Teixeira Rech, Dianer Nornberg Strelow, Leticia Devantier Kruger, Jose Sebastiao Santos Neto, Gustavo Bierhals Blodorn, Diego Alves, Cesar Augusto Bruning, Cristiani Folharini Bortolatto
Summary: This study aimed to evaluate the relationship between the antidepressant-like effect of 2-phenyl-3-(phenylselanyl)benzofuran (SeBZF1) and the glutamate pathway. The results showed that pretreatment of mice with drugs targeting glutamate receptors inhibited the antidepressant-like effect of SeBZF1. These findings contribute to a better understanding of the pharmacological effects of SeBZF1.
NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY
(2023)
Article
Neurosciences
Thiago Angelo Smaniotto, Angela Maria Casaril, Darling de Andrade Lourenco, Fernanda S. Sousa, Fabiana K. Seixas, Tiago Collares, Rafael Woloski, Luciano da Silva Pinto, Diego Alves, Lucielli Savegnago
Summary: Our study investigated the effects of intranasal administration of interleukin-4 (IL-4) on mice with depressive-like behavior induced by chronic unpredictable mild stress (CUMS). We found that IL-4 reversed the depressive behavior and regulated oxidative stress markers in the brain structures, suggesting its potential as an innovative strategy for major depression (MD) treatment.
PSYCHOPHARMACOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Mauricio Tavares Jacques, Viviane de Souza, Flavio Augusto Rocha Barbosa, Romulo Faria Santos Canto, Samantha Cristiane Lopes, Rui Daniel Prediger, Antonio Luiz Braga, Michael Aschner, Marcelo Farina
Summary: Oxidative glutamate toxicity is a harmful mechanism in ischemic stroke. Two new probucol analogues (C1 and C2) were designed and synthesized, and their effects against glutamate-induced neuronal oxidative toxicity were investigated. C2 showed the lowest toxicity and provided significant protection against glutamate-induced cytotoxicity both in vitro and in vivo. This study presents a promising neuroprotective drug for ischemic stroke.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Chemistry, Organic
Emilay B. T. Diogo, Fabio G. Delolo, Gabriela A. P. Graca, Esther R. S. Paz, icaro A. O. Bozzi, Renata Diniz, Juliano P. Passos, Tulio Matencio, Liane K. Soares, Diego Alves, Pedro M. S. Costa, Claudia Pessoa, Cynthia L. M. Pereira, Lutz Ackermann, Eufranio N. da Silva Junior
Summary: Undivided electrochemical cells are used to economically prepare sulphur-containing naphthoquinones through electrochemical sulphenylation of quinoidal compounds. This environmentally friendly and efficient protocol eliminates the need for chemical oxidants and enables the synthesis of desired molecules. It offers an efficient and versatile method for synthesizing cytotoxic quinones against cancer cell lines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Biochemistry & Molecular Biology
Gabriel Pereira da Costa, Gustavo Bierhals Blodorn, Angelita Manke Barcellos, Diego Alves
Summary: The importance of organoselenium compounds has been increasing in synthetic chemistry. They can serve as electrophiles, nucleophiles, and catalysts for organic transformations. The combination of inorganic and organic oxidants with organoselenium catalysts enables efficient, mild, and selective reactions.
Article
Neurosciences
Ana Claudia Funguetto-Ribeiro, Kelly Ayumi Nakama, Mikaela Peglow Pinz, Renata Leivas de Oliveira, Manoela do Sacramento, Flavia S. Oliveira Pereira, Simone Pinton, Ethel Antunes Wilhelm, Cristiane Luchese, Diego Alves, Daiana Silva avila, Sandra Elisa Haas
Summary: This study developed and investigated the effects of TQ-loaded polymeric nanocapsules (NCTQ) in an AD model, showing low toxicity and the potential to improve memory impairment.
Article
Chemistry, Multidisciplinary
Muhammad Saeed Ahmad, Abu Bakar Siddique, Muhammad Khalid, Akbar Ali, Muhammad Ashraf Shaheen, Muhammad Nawaz Tahir, Muhammad Imran, Ahmad Irfan, Muhammad Usman Khan, Marcio Weber Paixao
Summary: In this study, a one-pot synthesis of tetra-substituted imidazole was reported, and a series of metal complexes were obtained by reacting the synthesized imidazole with salts of 1(st) row transition metals. The synthesized compounds were characterized using spectroscopic and analytical techniques, and their antioxidant and antimicrobial activities were evaluated. The results showed that the metal complexes exhibited stronger antimicrobial activity compared to the ligand, and the ligand had better antioxidant activity than the metal complexes. Computational studies revealed a clear intra-molecular charge transfer in the ligand and its metal complexes.
Article
Chemistry, Multidisciplinary
Carlos V. Doerner, Jose S. S. Neto, Climei R. Cabreira, Sumbal Saba, Louis P. Sandjo, Jamal Rafique, Antonio L. Braga, Francisco F. de Assis
Summary: Here, an original and sustainable synthetic methodology for the synthesis of 3-selanyl-isoflavones from 2-hydroxyphenyl enaminones and diorganoyl diselenides is presented. The reaction, promoted by trichloroisocyanuric acid and using ethanol as a solvent, proceeds in a one-pot manner under mild conditions. Using this protocol, 22 examples of 3-selanyl-isoflavones were prepared in yields ranging from 34% to 95%.
NEW JOURNAL OF CHEMISTRY
(2023)
