Article
Chemistry, Organic
Qiuyu Zhu, Yu Tang, Biao Yu
Summary: A catalytic glycosyl fluoride activation system using the GeCl2·dioxane-AgBF4 combination was developed, involving reversible activation of C-F bond and reversible chloride ion transfer. This system is easy to operate, proceeds at room temperature, and has a broad scope of substrates.
Article
Chemistry, Organic
Yoshiyuki Manabe, Takuya Matsumoto, Yuka Ikinaga, Yuya Tsutsui, Shota Sasaya, Yuichiro Kadonaga, Akihito Konishi, Makoto Yasuda, Tomoya Uto, Changhao Dai, Kumpei Yano, Atsushi Shimoyama, Ayana Matsuda, Koichi Fukase
Summary: The study found that catalytic glycosylations using BF3·Et2O could efficiently proceed without the use of dehydrating agents, in contrast to traditional reactions requiring excess Lewis acid and additives. Mechanistic studies showed that chemical species formed by the reaction of in situ generated HF and glass vessels are involved in the catalytic cycle.
Article
Chemistry, Physical
Tong Li, Tianlu Li, Haoru Zhuang, Fengshan Wang, Richard R. Schmidt, Peng Peng
Summary: Stereo- and regioselective glycosidation remains a significant challenge in carbohydrate chemistry. Acid-base catalysis, particularly in O-glycosyl trichloroacetimidate activation, offers an alternative pathway with increased proton acidity and oxygen nucleophilicity for selective glycosidation. Platinum(IV) chloride serves as an ideal catalyst due to its weak Lewis acid properties and bidentate ligation capacity, enabling predominantly beta-configuration glycosidation products and regioselectivity in various carbohydrate acceptor moieties.
Article
Geochemistry & Geophysics
Anirban Basu, Kathrin Schilling, Alex N. Halliday, Naomi Wasserman, Thomas M. Johnson
Summary: Tellurium released into the environment from mining and industrial activities can contaminate soil, water, and food sources. This study explores the removal of Te(IV) from aqueous environments by siderite, revealing effective immobilization of Te(IV) through pseudo-first order kinetics and minimal isotope fractionation controlled by Te(IV) adsorption and reduction.
Article
Chemistry, Organic
Maria A. Boulogeorgou, Alexandros Toskas, John K. Gallos, Christos I. Stathakis
Summary: A direct and practical method for oxidative anomeric O-glycosylation of glycosyl iodides with various alcohols as glycosyl acceptors is presented. By using phenyliodine(iii) diacetate (PIDA) as the promoter, the reaction can be carried out at ambient temperature, providing environmentally friendly and operationally simple access to 1,2-trans-O-glycosides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Maxim Musalov, Vladimir A. Potapov, Vladimir A. Yakimov, Maria Musalova, Arkady A. Maylyan, Sergey Zinchenko, Svetlana Amosova
Summary: The regioselective synthesis of novel functionalized condensed organochalcogen compounds was achieved through chalcogenocyclofunctionalization reactions based on chalcogen halides and natural products thymol and carvacrol. Various selenides, sulfides, telluranes, and ditellurides were successfully synthesized with high yields, highlighting the distinct reactivity of sulfur, selenium, and tellurium halides in the reactions.
Article
Chemistry, Organic
Rongkun Liu, Qingting Hua, Qixin Lou, Jiazhe Wang, Xiaona Li, Zhi Ma, You Yang
Summary: The study presents an efficient glycosidation method using NIS/TMSOTf as promoters and glycosyl ortho-hexynylbenzoates as donors for the synthesis of O-glycosides and nucleosides. This approach offers mild reaction conditions, cheap promoters, wide substrate scope, and good to excellent yields. Additionally, the method shows promise in constructing challenging O- and N-glycosidic linkages and synthesizing oligosaccharides efficiently.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yu Yang, Nan Jiang, Yuling Mei, Zekun Ding, Jianbo Zhang
Summary: A sustainable magnetic core-shell nanocatalyst Fe3O4@C@Fe(III) was successfully used for the synthesis of a series of 2-nitro-2,3-unsaturated O-glycosides with high yields and stereoselectivity. The catalyst exhibited wide substrate applicability, including different kinds of alcohols and structurally complex acceptors. In addition, the catalyst could be easily separated and reused multiple times without significant decrease in catalytic performance.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Ramu Sridhar Perali, Umamaheswara Rao Boddu, Drisya Chittadi Sankar
Summary: The study presents a simple and efficient strategy for the regio- and stereoselective synthesis of carbon-branched sugar derivatives. By implementing Wittig rearrangement on substrates derived from various glycals and 3-O-alkenyl glycals through Ferrier rearrangement, a highly selective [1,2]- or [2,3]-Wittig rearrangement is revealed, providing a novel class of stereodefined 3-C-branched glycals and C-glycosides that are otherwise difficult to obtain.
Article
Chemistry, Organic
Nicholas W. See, Xiaowen Xu, Vito Ferro
Summary: A safe and operationally simple method for the preparation of fi-D-glycosyl fluorides has been presented, demonstrating the facile, high-yielding, and diastereoselective conversions of 2-O-acyl thioglycosides to fi-D- and other 1,2-trans glycosyl fluorides through a precise combination of XtalFluor-M, N-bromosuccinimide, and Et3N·3HF. The roles of these reagents and their interplay on fluorination stereoselectivity are dissected in this study.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hongkui Zhang, Jiajia He, Yayun Chen, Cheng Zhuang, Chunhui Jiang, Kai Xiao, Zhishan Su, Xiaoyu Ren, Tianli Wang
Summary: Chiral (dihydro)furo-fused heterocycles are important structural elements in various natural products, functional materials, and pharmaceuticals. An efficient method using dipeptide-phosphonium salt catalysis has been developed to prepare structurally fused heterocyclic compounds with high yields and excellent stereoselectivities. Mechanistic studies revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of the reaction, particularly through initial ketone alpha-addition and hydrogen-bonding interactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Manman Cheng, Haikun Zhang, Yan Li, Wenhao Chen
Summary: This study reported a riboflavin-involved pathway for the reduction of Se(IV) and Te(IV) by marine Shewanella sp. FDL-2, which enhances electron transfer efficiency and promotes the bioreduction of Se(IV)/Te(IV).
Article
Chemistry, Medicinal
Mikhailo Slivka, Maksym Fizer, Ruslan Mariychuk, Marek Ostafin, Olexander Moyzesh, Galyna Koval, Oksana Holovko-Kamoshenkova, Ivan Rusyn, Vasyl Lendel
Summary: This study evaluated the antimicrobial potential of new derivatives of thiazole-triazoles. Effective, easy-to-implement and low-cost routes for their synthesis were reported. The microbiological evaluation showed that two compounds exhibited high bactericidal activity and one compound showed high fungicidal activity. These products or their derivatives may have practical benefits as bactericidal and fungicidal agents.
LETTERS IN DRUG DESIGN & DISCOVERY
(2022)
Article
Chemistry, Physical
Peizhen Yang, Zhenhua Cao, Yuhan Long, Dongfang Liu, Wenli Huang, Sihui Zhan, Miao Li
Summary: Generating singlet oxygen (O-1(2)) on Cu SACs with different electronic structures has potential for selective degradation of contaminants in complex wastewater. The electronic structure of the Cu-O2B site affects the selectivity of O-1(2) generation, and the Cu-O2B moiety exhibits superior catalytic activity for PMS activation and ciprofloxacin degradation. The asymmetric Cu-O2B site accelerates faster electron transfer and O-O bond stretching, lowering the energy barrier of key intermediates towards O-1(2) generation.
Article
Chemistry, Inorganic & Nuclear
Rhys P. King, John M. Dyke, William Levason, Gillian Reid
Summary: The reaction of SiI4 and PMe3 in n-hexane produced a yellow salt, [SiI3(PMe3)2]I, which was characterized by its X-ray structure. In this structure, the silicon ion exhibits a trigonal bipyramidal geometry with trans-phosphines. This is in contrast to the six-coordination found in trans-[SiX4(PMe3)2] (X = Cl, Br) complexes.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Juliana L. L. F. Regueira, Claudio R. Dantas, Jucleiton J. R. de Freitas, Anderson J. F. Santos da Silva, Joao R. Freitas Filho, Paulo H. Menezes, Juliano C. R. Freitas
SYNTHESIS-STUTTGART
(2016)
Article
Chemistry, Organic
Jucleiton J. R. Freitas, Tulio R. Couto, Italo H. Cavalcanti, Juliano C. R. Freitas, Queila P. S. Barbosa, Roberta A. Oliveira
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Medicinal
Jonh A. M. Santos, Cosme S. Santos, Claudia L. A. Almeida, Thiago D. S. Silva, Joao R. Freitas Filho, Gardenia C. G. Militao, Teresinha G. da Silva, Carlos H. B. da Cruz, Juliano C. R. Freitas, Paulo H. Menezes
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2017)
Article
Chemistry, Organic
Arisson Tranquilino, Silvia R. C. P. Andrade, Ana Paula M. da Silva, Paulo H. Menezes, Roberta A. Oliveira
TETRAHEDRON LETTERS
(2017)
Article
Chemistry, Physical
Gilson B. da Silva, Paulo H. Menezes, Ivani Malvestiti, Eduardo H. L. Falcao, Severino Alves, Jarosiaw Chojnacki, Fausthon F. da Silva
JOURNAL OF MOLECULAR STRUCTURE
(2018)
Article
Chemistry, Multidisciplinary
Renato L. Silva, Cosme S. Santos, Jonh A. M. Santos, Roberta A. Oliveira, Paulo H. Menezes, Juliano C. R. Freitas
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Applied
Antonio A. Soares-Paulino, Lilian Giroldo, Gizele Celante, Elisabete Oliveira, Sergio M. Santos, Ricardo F. Mendes, Filipe A. Almeida Paz, Alexandre M. Fioroto, Pedro Oliveira, Silvia H. P. Serrano, Carlos Lodeiro, Alcindo A. Dos Santos
Article
Chemistry, Organic
Jucleiton J. R. Freitas, Queila P. S. B. Freitas, Silvia R. C. P. Andrade, Juliano C. R. Freitas, Roberta A. Oliveira, Paulo H. Menezes
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Igor M. R. Moura, Arisson Tranquilino, Barbara G. Satiro, Ricardo O. Silva, Diogo De Oliveira-Silva, Roberta A. Oliveira, Paulo H. Menezes
Summary: A novel strategy for synthesizing sulfides and selenides from phosphonium salts and thio- or selenesulfonates is described, without the need for metals, reactive species, or anhydrous conditions. Different products were obtained when using phosphoranes in the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Agriculture, Multidisciplinary
Maria Veronica Sales Barbosa, Alana Karoline Penha Nascimento, Rodrigo Ribeiro Alves Caiana, Cosme Silva Santos, Wylly Araujo de Oliveira, Paulo Henrique Menezes, Juliano Carlo Rufino Freitas
Summary: The study synthesized new O-alkylamidoximes and evaluated their antifungal activity, showing moderate activity but opening up new possibilities for the development of more active antifungal agents.
BIOSCIENCE JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Romario Jonas Oliveira, Cosme Silva Santos, Rodrigo Ribeiro Alves Caiana, Kleber Juvenal Silva Farias, Renato Ferreira Almeida Junior, Paula Renata Lima Machado, Antonio Augusto Soares-Paulino, Paulo Henrique Menezes, Juliano Carlo Rufino Freitas
Summary: In this study, O-alkylaryl amidoximes were designed and synthesized as antiproliferative agents targeting PARP-1. The compounds exhibited in vitro antineoplastic activity against MCF-7 and Caco-2 cells, with one compound showing selective toxicity against VERO cells. These synthesized compounds show potential for further development as new antiproliferative drugs.
Article
Chemistry, Multidisciplinary
Jonh A. M. Santos, Claudia L. A. A. Santos, Joao R. Freitas Filho, Paulo H. Menezes, Juliano C. R. Freitas
Summary: Polyacetylene glycosides (PAGs) are a small class of secondary metabolites characterized by the presence of a sugar unit connected to a polyacetylene. These compounds are found in fungi, seaweed, and plants, and exhibit a wide range of biological and pharmacological activities, leading to exponential growth in literature on these compounds in recent years.
Article
Chemistry, Organic
Danilo Galdino, Jadielson C. Lima, Dmistocles A. Vicente, Paulo H. Menezes, Marcelo Navarro
Summary: This study presents an efficient strategy for the synthesis of sulfones from organic halides and sodium salts of sulfinic acids using graphite powder as a reusable catalyst and water as a solvent at room temperature. The method demonstrates a broad substrate scope, high functional group tolerance, easy extraction conditions, and isolated products without the need for further purification.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dmistocles A. Vicente, Danilo Galdino, Marcelo Navarro, Paulo H. Menezes
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
