Article
Chemistry, Organic
Huan Zhang, Haiwen Xiao, Feng Jiang, Yewen Fang, Lin Zhu, Chaozhong Li
Summary: The copper-catalyzed reaction involving arylcyclopropanes, N-fluorobis(arenesulfony)imides, and (bpy)Zn(CF3)(2) at room temperature provides the corresponding ring-opening 1,3-aminotrifluoromethylation products in satisfactory yields. The protocol is highly regioselective, offering a convenient entry to gamma-trifluoromethylated amines. A proposed mechanism suggests the trifluoromethylation of benzyl radicals.
Article
Chemistry, Medicinal
Wen-Yun Hsueh, Ying-Shuan E. Lee, Min-Sian Huang, Chin-Hung Lai, Yu-Sheng Gao, Jo-Chu Lin, Yu-Fen Chen, Chih-Lin Chang, Shan-Yen Chou, Shyh-Fong Chen, Yann-Yu Lu, Lien-Hsiang Chang, Shu Fu Lin, Yu-Hsiang Lin, Pi-Chen Hsu, Win-Yin Wei, Ya-Chi Huang, Yi-Feng Kao, Li-Wei Teng, Hung-Huang Liu, Ying-Chou Chen, Ta-Tung Yuan, Ya-Wen Chan, Po-Hsun Huang, Yu-Ting Chao, Shin-Yi Huang, Bo-Han Jian, Hsin-Yi Huang, Sheng-Chuan Yang, Tzu-Hao Lo, Guan-Ru Huang, Shao-Yun Wang, Her-Sheng Lin, Shih-Hsien Chuang, Jiann-Jyh Huang
Summary: This paper presents a novel cascade reaction for the synthesis of target products and demonstrates its application in total synthesis of natural products and anticancer activity. Further optimization of the products showed inhibitory activity against DNA topoisomerase-I, indicating potential anticancer effects.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Ankun Li, Xiaoxing Wang, Yuqing Liu, Delong Hao, Xia Zhao, Kui Lu
Summary: We have developed a ring-opening trifluoromethylthiolation of cyclopropanols using Cu(OAc)(2) as the catalyst. Furthermore, this strategy has been successfully applied to achieve the trifluoromethylselenolation of cyclopropanols with Se-(trifluoromethyl) 4-methoxybenzenesulfonoselenoate, leading to the synthesis of beta-SeCF3-substituted carbonyl compounds for the first time. The wide substrate scope, easily accessible reagents, and cost-effective catalyst make this protocol an alternative and efficient method for the synthesis of beta-SCF3-substituted or beta-SeCF3-substituted carbonyl compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Bang-Hong Zhang, Wen Bao, Fu Cheng, Ke-Yang Yu, Jia-Xuan Wang, Zi-Hao Zhang, Long-Jun Dong, Ze-Sen Xue, Dao-Yong Zhu, Xue-Tao Xu, Shao-Hua Wang
Summary: A Rh(I)-catalyzed [5 + 2]/[2 + 2] cycloaddition cascade has been developed to efficiently form a complex and highly strained [4-5-6-7] tetracyclic framework with good yields and excellent diastereoselectivities. The formation of three rings, three C-C bonds, and four contiguous stereocenters is achieved through the readily construction of rare sterically congested multi-substituted cyclobutanes using Michael addition and a Mannich reaction cascade.
Article
Chemistry, Organic
Bang-Hong Zhang, Wen Bao, Fu Cheng, Ke-Yang Yu, Jia-Xuan Wang, Zi-Hao Zhang, Long-Jun Dong, Ze-Sen Xue, Dao-Yong Zhu, Xue-Tao Xu, Shao-Hua Wang
Summary: A Rh(I)-catalyzed [5 + 2]/[2 + 2] cycloaddition cascade was developed to synthesize a complex and highly strained [4-5-6-7] tetracyclic framework with high yield and diastereoselectivity. Three rings, three C-C bonds, and four contiguous stereocenters were efficiently formed during the transformation. Mechanistically, the sterically congested multi-substituted cyclobutanes were readily constructed through a Michael addition and Mannich reaction cascade.
Article
Chemistry, Organic
Karthick Govindan, Tamilselvan Duraisamy, Alageswaran Jayaram, Gopal Chandru Senadi, Wei-Yu Lin
Summary: A simple and environmentally friendly copper-catalyzed assembly method is reported for the synthesis of quinazolinone and indazolone derivatives in a single protocol, showing good scalability. This method uses DMF as a reaction solvent and one carbon synthon for heterocyclic ring construction, featuring base-free and Bronsted acid free conditions with broad synthetic scope.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Physical
Weiguang Yang, Zitong Zhou, Yu Zhao, Danyang Luo, Xiai Luo, Hui Luo, Liao Cui, Li Li
Summary: A copper-catalyzed tandem reaction was developed to synthesize functionalized oxazines under mild conditions. The reaction involves N-sulfonyl acylketenimines undergoing cycloaddition with imines to form a series of 1,3-oxazine derivatives successfully.
Article
Chemistry, Organic
Wei Wu, Shunli Wen, Xinyu Zhang, Qi Lin, Zhiqiang Weng
Summary: A highly efficient and regioselective synthesis of highly substituted 2-trifluoromethyl pyrrole derivatives is reported via a silver-catalyzed cyclization of vinyl azides with ethyl 4,4,4-trifluoro-3-oxobutanoate. Various types of alpha-(heteo)aryl, alkyl, alpha-aryl, and alpha,beta-disubstituted vinyl azides can participate in this transformation. The proposed reaction mechanism involves the addition of in situ generated 2H-azirine to the diketone species, followed by intramolecular addition, N-C-1 cleavage, and elimination.
Article
Chemistry, Applied
Xueying Zhou, Shanshan Shi, Luya Chen, Ge Wu, Yunfei Ma
Summary: This study describes a copper-catalyzed oxidative carboamination of maleimides with alkyl amines and alpha-bromo carboxylates. These multicomponent reactions demonstrate good functional group compatibility and are suitable for the late-stage modification of various neuroprotective agents, providing a direct pathway for the synthesis of 3-carbo-4-amino maleimides.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Yu-Ting Gao, Shao-Dong Liu, Liang Cheng, Li Liu
Summary: This study reports a metal-free 2-selenylation reaction of tryptophan derivatives with high yields, tolerating various functional groups and showing no racemization under the use of iodide as the catalyst and oxone as the oxidant.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Noriyoshi Arai
Summary: Irradiation of N-(omega-alkenyl)isocarbostyrils with LED emitting 455 nm light in the presence of an iridium photocatalyst selectively yielded cyclobutane-fused benzo[b]quinolizine derivatives in high yields. The use of only 1 mol % catalyst loading was sufficient to obtain high yields of the products within a convenient reaction time in many cases. The reaction likely proceeds via a stepwise [2 + 2] cycloaddition through a triplet biradical intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Rana Chatterjee, Mohanreddy Pothireddy, Rambabu Dandela
Summary: An efficient copper-catalyzed intermolecular decarboxylative cascade cyclization was developed using readily accessible starting materials and less-expensive reagents. A one-pot reaction of an aryl aldehyde, an aniline, and acrylic acid allows for the direct synthesis of 2-substituted quinolines through sequential C-N and C-C bond formation. The three-component, one-pot, domino strategy demonstrates promising chemo- and regioselectivity, high functional-group tolerance, excellent yields, a radical reaction pathway, and aerobic reaction conditions.
Article
Chemistry, Organic
Margherita Zanini, Andrea Cataffo, Antonio M. Echavarren
Summary: A method for the synthesis of cyclobutanones through gold(I)-catalyzed [2 + 2] cycloaddition of ynol ethers with alkenes has been developed. Additionally, it was found that internal aryl ynol ethers can undergo (4 + 2) cycloaddition reaction with alkenes leading to the corresponding chromanes.
Article
Chemistry, Organic
Noriyoshi Arai
Summary: Irradiating N-(omega-alkenyl)isocarbostyrils with iridium photocatalyst under 455 nm LED light results in stereoselective synthesis of cyclobutane-fused benzo[b]quinolizine derivatives with high yields. A catalyst loading of just 1 mol% is sufficient for producing high yields of products within a reasonable reaction time in most cases. The reaction proceeds through a stepwise [2 + 2] cycloaddition mechanism involving a triplet biradical intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
A. Srinivasulu, D. Vani, G. Sathish Kumar, B. Shantharjun, Kapil Chahal, Balasubramanian Sridhar, K. Rajender Reddy
Summary: This study reports a method for the synthesis of pharmaceutically interested compounds by activating N-alkyl formamide using a copper/oxidant system via a tandem/domino reaction pathway to construct C-N/C-O bond formation, without the need for toxic chemicals.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Nandor Gyorfi, Emese Farkas, Norbert Nemet, Csaba Weber, Zoltan Novak, Andras Kotschy
Article
Chemistry, Organic
Reka Adamik, Tamas Foldesi, Zoltan Novak
Correction
Chemistry, Organic
Reka Adamik, Tamas Foldesi, Zoltan Novak
Article
Multidisciplinary Sciences
Ferenc Beke, Adam Meszaros, Agnes Toth, Bence Bela Botlik, Zoltan Novak
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Janos T. Csenki, Adam Meszaros, Zsombor Gonda, Zoltan Novak
Summary: A stereoselective N-trifluoropropenylation method based on a bench-stable trifluoropropenyl iodonium salt is described, enabling straightforward trifluoropropenylation of various N-heterocycles under mild reaction conditions to provide trifluoromethyl enamine type moieties with high stereoselectivity and efficiency.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Balint Varga, Balazs L. Toth, Ferenc Beke, Janos T. Csenki, Andras Kotschy, Zoltan Novak
Summary: A novel fluoroalkyl iodide was synthesized from refrigerant gas HFO-1234yf as a cheap starting material in a simple and scalable process, demonstrating its applicability in a metal-free photocatalytic ATRA reaction to synthesize valuable fluoroalkylated vinyl iodides and its transformability in cross-coupling chemistry to obtain conjugated systems.
Review
Chemistry, Organic
Balint Varga, Janos T. Csenki, Balazs L. Toth, Ferenc Beke, Zoltan Novak, Andras Kotschy
Summary: Hydrofluoroolefin (HFO) gases are advanced cooling agents used in household and industrial applications, drawing attention from organic chemists for their structural benefits. They serve as starting materials for synthesizing fluorine-containing organic molecules, which are important building blocks and reagents for diverse syntheses.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Zsombor Gonda, Tamas Foldesi, Balint Nagy, Zoltan Novak
Summary: In this study, the modular synthesis of carbazole functionalized phthalimides and their application as catalysts in selected photocatalytic transformations were reported. The synthetic approach allowed for a high variability of phthalimides, with the introduction of carbazoles into the phthalimide framework through aromatic nucleophilic substitution. The carbazolyl phthalimides showed attractive and comparable activity to known 4-CzIPN and noble metal complexes in four different photocatalytic transformations.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Applied
Balazs L. Toth, Gergo Salyi, Attila Domjan, Orsolya Egyed, Attila Benyei, Zsombor Gonda, Zoltan Novak
Summary: The study reports a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds utilizing palladium-catalyzed ortho C-H activation reaction of aniline derivatives. The use of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allows mild reaction conditions, and feasibility has been demonstrated through over 50 examples.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Multidisciplinary
Reka Adamik, Balazs Buchholcz, Ferenc Darvas, Gellert Sipos, Zoltan Novak
Summary: This review provides a conceptual and critical summary of micellar synthesis possibilities that are well suited to DEL synthesis, as well as discussion of existing examples of micellar DEL approaches and selection of micellar organic transformations fundamentally suitable for DEL.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Editorial Material
Chemistry, Physical
Zoltan Novak, Reka Adamik, Janos T. Csenki, Ferenc Beke, Regina Gavaldik, Balint Varga, Balint Nagy, Zoltan May, Janos Daru, Zsombor Gonda, Gergely L. Tolnai
Article
Chemistry, Multidisciplinary
Janos T. Csenki, Balazs L. Toth, Ferenc Beke, Balint Varga, Peter P. Feher, Andras Stirling, Zsuzsanna Czegeny, Attila Benyei, Zoltan Novak
Summary: This study reports a novel dyotropic rearrangement process involving the migration of iodine atoms in alkyl fragments, demonstrated through experimental and DFT studies. A new fluoroalkyl iodonium reagent was designed and synthesized using the dyotropic rearrangement, showing excellent fluoroalkylation activity towards various amines and nitrogen heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Michaela Wernik, Gellert Sipos, Balazs Buchholcz, Ferenc Darvas, Zoltan Novak, Sandor B. Oetvoes, C. Oliver Kappe
Summary: The study demonstrates the successful application of an oscillatory plug flow reactor in enabling heterogeneous catalytic reductive aminations in aqueous micellar media, enhancing mass transport and facilitating process simplicity, stability, and scalability. The method allows for the successful transformation of a broad range of substrates, including amino acid derivatives, under relatively mild conditions, utilizing only small amounts of Pd/C as a readily available heterogeneous catalyst, with the recyclability of the catalyst and reaction media also demonstrated.
Article
Chemistry, Multidisciplinary
Louise Ruyet, Maria I. Lapuh, Vijay S. Koshti, Tamas Foldesi, Philippe Jubault, Thomas Poisson, Zoltan Novak, Tatiana Besset
Summary: A method for the straightforward 2,2,2-trifluoroethylation of acrylamides via Pd-catalyzed C-H bond activation using a fluorinated hypervalent iodine reagent as a coupling partner has been reported. This additive-free approach allows for the stereoselective synthesis of Z-2,2,2-trifluoroethylated acrylamides under mild reaction conditions, showcasing good functional group tolerance and providing mechanistic insights into the transformation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Balazs L. Toth, Anna Monory, Orsolya Egyed, Attila Domjan, Attila Benyei, Balint Szathury, Zoltan Novak, Andras Stirling
Summary: The study introduces a substrate-only-based model to interpret the influence of neighboring groups on the directing group in ortho-C-H bond activation reactions, defining the Ortho Effect (OE) for such situations. Simple descriptors like torsion angle and torsional energy are used to predict and explain substrate reactivity in directed C-H activation reactions. Structural and energetic criteria are set to evaluate the efficiency of the metalation step, providing guidance for organic chemists and predictions for reaction conditions for selected directing groups.
