Article
Chemistry, Organic
Ying Yang, Ya-Nan Jiang, Zhi-Yi Lin, Jia-Hao Zeng, Zhi-Kai Liu, Zhuang-Ping Zhan
Summary: The use of a porous organic polymer as a heterogeneous ligand in 1,3-diyne hydrosilylation reaction can significantly increase the selectivity and efficiency, showing promising prospects for industrial applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Inorganic & Nuclear
Lu Dong, Linke Yu, Xueli Sun, Xiongkai Tang, Xuexin You, Jiaqi Tang, Zi-Ang Nan, Dongxu Cao, Yanyuan Jia, Simin Li, Fengyu Li, Shuo Guo, Hui Shen
Summary: We report a stable gold-copper alloy nanocluster with high catalytic performance. The nanocluster exhibits high thermal stability and contains rich uncoordinated copper sites, which contribute to its extremely high catalytic activity in C-O coupling reactions. This finding is of great significance for understanding the underlying rationale of ligand-functionalized metal nanocatalysts.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Zhaoyang Cheng, Jun Guo, Yufeng Sun, Yushan Zheng, Zhehong Zhou, Zhan Lu
Summary: This study presents a controllable cobalt-catalyzed sequential hydrosilylation/hydroboration reaction of arylacetylenes, achieving high regioselectivities for all possible regio-outcomes. Adjusting the ligands of cobalt catalysts combined with dual catalysis relay strategy is crucial for achieving regio-chemistry control, which may inspire further exploration in diversity-oriented synthesis involving multiple additions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Lina Cai, Qihong Lai, Lele Zhang, Guotao Xue, Yirui Zhang, Na He, Mingqiang Huang, Shirong Hu, Shunyou Cai
Summary: This study presents an efficient and practical lanthanum-catalyzed reaction method for continuous epoxy-ring opening and oxidative dehydrogenative lactonization under visible-light irradiation. The lanthanum catalyst acts as both a Lewis acid and a photocatalyst in this reaction, eliminating the need for additional photocatalysts. The method allows for convenient preparation of isochromanones with oxygen-containing spirocyclic structural units.
Article
Chemistry, Organic
Huaxin Zhang, Yongge Xiong, Jiang Bai, Ruchun Yang, Xian-Rong Song, Qiang Xiao
Summary: We introduce a highly efficient and practical method for synthesizing gem-dibromo 1,3-oxazines through 6-endo-dig cyclization of propargylic amides, using N-bromosuccinimide (NBS) as an electrophilic source. This metal-free reaction can be carried out under mild conditions, showing good compatibility with various functional groups and providing excellent yields of the desired products. Mechanistic studies indicate that the reaction proceeds through a double electrophilic attack of NBS on the propargylic amide substrate.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Qingheng Lai, Oleg Ozerov
Summary: The catalytic dehydrogenative diboration (DHDB) of alkyne with HBpin was successfully achieved using Ir precursors under CO atmosphere, with higher selectivity in less polar solvents and higher CO pressure. the addition of a catalytic amount of tBuNC further improved the selectivity, leading to isolation of some DHDB products on the preparative scale.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Qimin Wu, Qi Zhang, Shuxin Yin, Aijun Lin, Shang Gao, Hequan Yao
Summary: A platinum-catalyzed atroposelective hydrosilylation of unactivated internal alkynes has been reported for the first time. By using L1 as a chiral ligand, various axially chiral styrenes were obtained with excellent enantioselectivities and high E-selectivities. Control experiments showed that NH-arylamide groups have significant effects on yields and enantioselectivities, and they can act as directing groups. The potential applications of the products were demonstrated through transformations of the amide motifs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Konstantin V. Deriabin, Ekaterina A. Golovenko, Nikita S. Antonov, Sergey V. Baykov, Vadim P. Boyarskiy, Regina M. Islamova
Summary: A platinum polymer catalyst (Pt-PDMS) was synthesized by immobilizing a platinum catalytic complex in a polysiloxane chain using an azide-alkyne CuAAC cycloaddition. Insoluble Pt-PDMS can be used as an effective heterogeneous macrocatalyst for Si-O dehydrocoupling. Pt-PDMS is easy to recover, purify, and reuse again for heterogeneous catalysis.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Malgorzata Bolt, Aleksandra Mermela, Patrycja Zak
Summary: This study describes the synthesis and characterization of a new bifunctional N-heterocyclic carbene precursor with sterically expanded substituents. The obtained NHC is used in the catalytic system for hydrosilylation of internal alkynes, providing a fully selective and efficient reaction under mild conditions in the presence of air. Comparative analysis with analogs based on monofunctional NHC ligands demonstrates that the presence of two metal atoms and the proper design of the steric environment around the metal center significantly enhance the catalytic activity in the hydrosilylation process.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Nikolay V. V. Shcherbakov, Polina F. F. Kotikova, Elena I. I. Chikunova, Dmitry V. V. Dar'in, Vadim Yu. Kukushkin, Alexey Yu. Dubovtsev
Summary: The gold-catalyzed interplay between ynamides and aminocarbonyls provides a pathway to 2-aminoquinolines. This modular annulation reaction occurs under mild conditions and is compatible with various functionalities. Unlike other gold-catalyzed methods, this approach allows for the use of diverse aminocarbonyl substrates and allows for the variation of substituents in the 4th position of the quinoline. The obtained heterocyclic products demonstrate synthetic potential through post-modifications of the quinoline backbone and peripheral substituents.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Leandro Duarte de Almeida, Hongli Wang, Kathrin Junge, Xinjiang Cui, Matthias Beller
Summary: This minireview discusses the use of homogeneous noble metal catalysts and earth-abundant transition metals/heterogeneous catalysts in hydrosilylation reactions, highlighting the growing interest in more sustainable and economic catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Ria Ayu Pramudita, Ken Motokura
Summary: This article presents the current development of utilizing hydrosilanes in the chemical reduction of CO2, with a focus on organic catalysts. The use of heterogeneous organocatalysts with precisely designed active sites is emphasized for their recyclability and higher efficiency in these transformations.
Article
Chemistry, Multidisciplinary
Shashank P. Sancheti, Yukta Singh, Manoj V. Mane, Nitin T. Patil
Summary: This study reports the first gold-catalyzed 1,2-dicarbofunctionalization of alkynes using organohalides as non-prefunctionalized coupling partners. The mechanism of the reaction involves an oxidative addition/pi-activation pathway, which is different from the migratory insertion/cis-trans isomerization pathway observed in other transition metal catalysis. Mechanistic investigations including experiments, NMR studies, HR-MSMS analyses, and DFT calculations provide strong support for the proposed mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zhijun Li, Xiaowen Lu, Rufang Zhao, Siqi Ji, Mingyang Zhang, J. Hugh Horton, Yang Wang, Qian Xu, Junfa Zhu
Summary: Researchers have developed an efficient molten-salt-assisted approach to create atomically dispersed cobalt atoms supported over vanadium pentoxide layered material. This cobalt single-atom catalyst achieves extraordinary catalytic efficiency in the dehydrogenative coupling reaction of alcohols and amines, with high selectivity and conversion. Density functional theory calculations confirm the optimized coordination environment and strong metal-support interaction contribute significantly to the activation of reactants.
Article
Chemistry, Organic
Xinyu Chen, Yi-Guo Huang, Wei-Qiang Zhong, Jing-Mei Huang
Summary: An electrochemical method for the decarboxylative silylation of alpha,beta-unsaturated carboxylic acids has been developed with satisfactory yields and excellent selectivities. Mechanistic studies reveal that NHPI mediates the formation of silyl radicals by generating the HAT reagent PINO via MS-CPET.
Article
Chemistry, Organic
Michael G. Kallitsakis, Dimitris I. Ioannou, Michael A. Terzidis, George E. Kostakis, Ioannis N. Lykakis
Article
Chemistry, Organic
Dimitris I. Ioannou, Dimitra K. Gioftsidou, Vasiliki E. Tsina, Michael G. Kallitsakis, Antonios G. Hatzidimitriou, Michael A. Terzidis, Panagiotis A. Angaridis, Ioannis N. Lykakis
Summary: A new study reports an efficient catalytic protocol using methylhydrazine as a reducing agent and tris(N-heterocyclic thioamidate) Co(III) complex as a catalyst to selectively reduce nitroarenes to arylamines with high yields and chemoselectivity. Preliminary investigations suggest a cooperative action of methylhydrazine and the catalyst through a coordination activation pathway, leading to the formation of a reduced cobalt species responsible for the catalytic transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Marina A. Tzani, Catherine Gabriel, Ioannis N. Lykakis
Article
Chemistry, Organic
Dimitrios Andreou, Nsikak B. Essien, Cristina Pubill-Ulldemolins, Michael A. Terzidis, Athanasios N. Papadopoulos, George E. Kostakis, Ioannis N. Lykakis
Summary: A copper-mediated method was developed for the synthesis of seven-membered-ring fused pyrroles, allowing for the tolerance of various functional groups in the derivatives and exhibiting high antioxidant activity in selected examples. These rare 7-mrFPs can now be accessed on a millimolar scale.
Article
Chemistry, Organic
Marina A. Tzani, Stella Fountoulaki, Ioannis N. Lykakis
Summary: In this study, we investigated the catalytic efficacy of silicotungstic acid as a polyoxometalate towards the synthesis of trans-DACPs. Our results demonstrate that this method offers a highly efficient and versatile approach for the synthesis of trans-DACPs with excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Marina A. Tzani, Dimitra K. Gioftsidou, Michael G. Kallitsakis, Nikolaos V. Pliatsios, Natasa P. Kalogiouri, Panagiotis A. Angaridis, Ioannis N. Lykakis, Michael A. Terzidis
Summary: This review explores the mechanisms and applications of chemiluminescence, including both direct and indirect production modes. It discusses the characteristics of chemical reactions and CL mechanisms, summarizes methods to enhance CL efficiency, and examines the role of CL in the development of therapeutic platforms.
Article
Chemistry, Multidisciplinary
Vassiliki Daikopoulou, Euaggelia Skliri, Eirini D. Koutsouroubi, Gerasimos S. Armatas, Ioannis N. Lykakis
Summary: This study reports the synthesis and catalytic application of mesoporous Au-loaded Mn3O4 nanoparticle assemblies with different Au contents for the selective oxidation of anilines into nitroarenes. The results show that Au/Mn3O4 MNAs containing 0.5 wt % Au exhibit the best catalytic performance among different catalysts, leading to high yields and selectivity of the corresponding nitroarenes.
Article
Biochemistry & Molecular Biology
Domna Iordanidou, Michael G. Kallitsakis, Marina A. Tzani, Dimitris I. Ioannou, Tryfon Zarganes-Tzitzikas, Constantinos G. Neochoritis, Alexander Domling, Michael A. Terzidis, Ioannis N. Lykakis
Summary: This study reported the synthesis of 3,4-dihydroquinoxalin-2-ones through the selective reduction reaction catalyzed by supported gold nanoparticles. The reaction proceeded through heterogeneous transfer hydrogenation and intramolecular C-N transamidation, resulting in good functional-group tolerance and high yields.
Review
Chemistry, Physical
Jonathan Farhi, Ioannis N. Lykakis, George E. Kostakis
Summary: This study summarizes the multicomponent reaction of aldehydes, amines, and alkynes, known as A(3) coupling, and discusses the application and impact of metal-based catalytic systems in this transformation. By classifying substrates, synthetic methods, and various variables, a valuable database is created.
Article
Oncology
Ioanna Tremi, Sophia Havaki, Sofia Georgitsopoulou, Georgia Terzoudi, Ioannis N. Lykakis, George Iliakis, Vasilios Georgakilas, Vassilis G. Gorgoulis, Alexandros G. Georgakilas
Summary: In this study, gold nanoparticles were found to act as radiation sensitizers, significantly reducing the colony-forming ability of cancer cells and causing higher levels of DNA damage. The nanoparticles also affected cell cycle distribution and cellular senescence. Different cell lines and types of gold nanoparticles may alter the level of radiosensitization.
Article
Chemistry, Organic
Aleksander R. Bena, Evangelos G. Bakalbassis, Michail M. Sigalas, Ioannis N. Lykakis
Summary: We report a one-pot strategy for the synthesis of 3-carboxyl and 3-ketopyridines using readily available alkynes and propargylamine. The protocol is conducted in aqueous media and open-air conditions, and offers a broad substrate scope. Various aryl- and alkyl-substituted pyridines were successfully synthesized, including the natural product core 4-aza-fluorenone. Mechanistic studies support a domino hydroamination/pericyclic reaction pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Andriani G. G. Chaidali, Ioannis N. N. Lykakis
Summary: A facile green synthetic protocol for the synthesis of several substituted N-(pyridin-2-yl)imidates was reported. The method involved the in situ formation of alpha-iminonitriles under the Lewis acid catalysis and subsequent conversion into the desired imidates using Cs2CO3 in alcoholic media. The synthetic protocol was also scalable and successfully applied for the synthesis of N-heterocycles.
Article
Chemistry, Multidisciplinary
Marina A. Tzani, Ioannis N. Lykakis
Summary: We investigated the efficient synthesis method of a series of trans-N,N-4,5-substituted-diaminocyclopent-2-enones (trans-DACPs) from furfural and anilines through Gold(III) chloride (HAuCl4) mediation. The protocol only required a low amount of catalysts (1.5 mol%), open air conditions, no additives, and short reaction times, resulting in good to high yields of the desired trans-DACPs. The method was also applicable to secondary amines, providing the corresponding 4,5-diamino-cyclopent-2-enones in good yields. To the best of our knowledge, this is the first gold-mediated paradigm as an efficient catalyst for the formation of the cyclopentenones core-bearing C-N bonds under mild reaction conditions.
CHEMISTRY-SWITZERLAND
(2023)
Review
Chemistry, Organic
Andriani G. Chaidali, Ioannis N. Lykakis
Summary: This review presents recent synthetic approaches and diverse applications of imidates, which are used as intermediates in organic transformations and have potential catalytic effects in the synthesis of N-heterocycles, natural products, and metal complexes. Various organic compounds, including nitriles, isocyanides, and amides, can be easily converted to imidates through simple and flexible processes. The review provides a categorized and summarized exploration of the recent synthetic routes and applications of imidates in organic transformations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Michael G. Kallitsakis, Dimitra K. Gioftsidou, Marina A. Tzani, Panagiotis A. Angaridis, Michael A. Terzidis, Ioannis N. Lykakis
Summary: The newly developed photocatalyst [Cu(Xantphos)(neoc)]BF4 can effectively oxygenate cycloalkenes into allylic hydroperoxides or alcohols with high yields and chemoselectivity. This methodology has been successfully applied to the synthesis of various bioactive compounds and perfumery ingredients, showcasing fast and clean reaction processes.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
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.
