Article
Chemistry, Multidisciplinary
Fan Yu, Zhaoman Zhou, Jiajia Song, Yanying Zhao
Summary: This study rationalized the mechanism of Cu(I)-catalyzed 5-enamine-functionalized fully substituted 1,2,3-triazole synthesis using density functional theory (DFT) and multicomponent artificial force-induced reaction (MC-AFIR) methods. The research provided important mechanistic insights for the interrupted CuAAC reaction and identified the rate-determining step as the transmetalation process along the triplet state potential energy surface. Further predictions suggest the role of solvent and extra strong ligand coordination in competitive reactions.
Article
Chemistry, Organic
Yulia Krivolapova, Olesya A. Tomashenko, Liya D. Funt, Dar'ya Spiridonova, Mikhail S. Novikov, Alexander F. Khlebnikov
Summary: Azirine-triazole hybrids were selectively synthesized under different reaction conditions and the reaction mechanism and selectivity were discussed based on DFT calculations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Robby Vroemans, Sergio R. Ribone, Joice Thomas, Luc Van Meervelt, Thierry Ollevier, Wim Dehaen
Summary: A new method for preparing novel homochiral atropisomeric sulfanyl- and sulfoxide-substituted naphthyltriazoles is described in this study, providing a new pathway for stable 1,2,3-triazole-based atropisomers. Sixteen sulfanyl-substituted naphthyltriazoles were obtained via triazolization reaction, followed by monooxidation. The absolute configuration of the substituted naphthyltriazoles was determined using X-ray crystallography and confirmed with computational DFT calculations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Samuel Pearce, Juan Perez-Mercader
Summary: By integrating various chemical processes, simplification of PISA process and routes to complexity and adaptation in chemical systems can be achieved.
ACS CENTRAL SCIENCE
(2021)
Article
Chemistry, Organic
Yong-Ju Kwon, Sang-Gi Lee, Won-Suk Kim
Summary: Continuous flow synthesis of N-sulfonyl-1,2,3-triazoles for tandem relay Cu/Rh dual catalysis was developed. The reactions proceeded readily at 75°C under short residence time and 2.5 mol% of CuTC catalyst. Diversely functionalized N-sulfonyl and sulfamoyl triazoles were synthesized with yields ranging from 92% to 98%. Scalability of the process was demonstrated and the compatibility of Cu and Rh in a batch or continuous flow system was investigated.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yong-Ju Kwon, Sang-gi Lee, Won-Suk Kim
Summary: The continuous flow synthesis of N-sulfonyl-1,2,3triazoles, convenient reactive azavinyl carbene precursors, for tandem relay Cu/Rh dual catalysis has been developed. Most reactions proceeded at 75 degrees C with a short residence time of 13.09 min in the presence of 2.5 mol % of CuTC. Diversely functionalized N-sulfonyl and sulfamoyl triazoles were synthesized in yields ranging from 92 to 98%.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wan-Yu Chen, Wei-Han Lin, Chia-Jou Kuo, Chien-Fu Liang
Summary: N-Sulfonylthioimidate is converted to ketenimine under basic conditions. The reaction with vinyl/aryl azides induces dipolar cycloaddition to form 5-amino-1-vinyl/aryl-1,2,3-triazoles. The method boasts high efficiency, diverse product structures, favorable yields, and applicability to gram-scale operations.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Suguru Yoshida, Yuki Sakata, Yoshihiro Misawa, Takamoto Morita, Tomoko Kuribara, Harumi Ito, Yuka Koike, Isao Kii, Takamitsu Hosoya
Summary: Efficient consecutive formation of 1,2,3-triazoles using multiazide platforms has been achieved in this study. A four-step synthesis of tetrakis(triazoles) was successfully performed from a tetraazide platform molecule, based on the unique clickability of the 1-adamantyl azido group. This method was applied to the convergent synthesis of tetrafunctionalized probes in a modular synthetic manner.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Atul Kumar, Navaneet Kumar, Deepak Bhadoria
Summary: The first visible-light promoted and photocatalyst-free three-component reaction protocol has been developed to efficiently synthesize 4-functionalized 1,5-disubstituted 1,2,3-triazoles from terminal alkynes, aryl azides, and arylsulfinic acid sodium salts or arylsulfonyl hydrazides in an aqueous medium at room temperature. This reaction offers high regioselectivity, scalability, and good functional group tolerance among its advantages.
Article
Chemistry, Medicinal
Elena O. Shestakova, Sergey G. Il'yasov, Irina A. Shchurova, Vera S. Glukhacheva, Dmitri S. Il'yasov, Egor E. Zhukov, Arkady O. Bryzgalov, Tatiana G. Tolstikova, Yuri V. Gatilov
Summary: In this study, the reaction of 1,3-dipolar cycloaddition between 1,3-diazido-2-nitro-2-azapropane (DANP) and propargyl alcohol was investigated, and the optimal reaction conditions for the synthesis of 2-nitro-1,3-bis(4,4'-dihydroxymethyl)-1,2,3-triazolyl-2-azapropane (1) were identified. Additionally, the reactions between DANP and 1,5-diazido-3-nitrazapentane, as well as phenylacetylene, produced the corresponding 1,2,3-triazole derivatives. The synthesized compounds were characterized using various spectroscopic techniques and elemental analysis. The antiarrhythmic activity of compound 1 was evaluated, demonstrating dose-dependent effects, indicating its potential as a therapeutic agent.
Article
Chemistry, Organic
Chun Huang, Xiao Geng, Peng Zhao, You Zhou, Xiao-Xiao Yu, Li-Sheng Wang, Yan-Dong Wu, An-Xin Wu
Summary: This method uses p-toluenesulfonyl hydrazines and 1-aminopyridinium iodide as azide surrogates to prepare 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions, providing a novel route to NH-1,2,3-triazoles. Additionally, this approach offers a rapid and practical access to potent inhibitors of indoleamine 2,3-dioxygenase (IDO).
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
R. Rengasamy, J. Paul Raj, K. Vijayalakshmi, N. Punitha, M. Kesavan, M. Vajjiravel, Jebamalai Elangovan
Summary: A tunable synthesis of 1,4,5-trisubstituted 1,2,3-triazoles and enamines through [3+2] cycloaddition of activated olefins and organic azides is reported. Triazoles were obtained from benzylidene diketones and organic azides using copper oxide nanoparticle catalysis, while enamines were synthesized from benzylidene malonates and organic azides under solvent-free and catalyst-free conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Christopher R. Butler, Justin Bendesky, Allen Milton Schoffstall
Summary: Regioselective reactions are important in synthetic organic chemistry, as seen in the reduction of 1-substituted 1,2,3-triazole 4,5-diesters where the C(5) ester groups are more reactive and the presence of a beta-hydroxyl group on the N(1)-substituent enhances the reduction rate. The regioselectivity is attributed to lower electron densities in the C(5) and C(5) ester carbonyl carbon of the 1,2,3-triazole, especially in cases involving intramolecular hydrogen bonding.
Review
Chemistry, Organic
Dileep Kumar Singh
Summary: Among the various approaches in organic synthesis, the click chemistry protocol, also known as CuAAC reaction, is commonly used to connect different moieties in a single framework. This review focuses on the synthesis and photophysical studies of porphyrin conjugates with meso-substituted and 1,2,3-triazole-fused structures. The triazole ring serves as a spacer and an electron transfer bridge between the attached chromophores and the porphyrin.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Kseniya A. Bezlepkina, Sofia N. Ardabevskaia, Kseniia S. Klokova, Aleksei I. Ryzhkov, Dmitry A. Migulin, Fedor V. Drozdov, Georgij V. Cherkaev, Aziz M. Muzafarov, Sergey A. Milenin
Summary: Despite the presence of many methods for the preparation, functionalization, and vulcanization of polysiloxanes, the development of materials based on silicones still requires the introduction of new approaches that combine modern strategies such as atom-economical reactions and green chemistry principles. This work presents modern approaches to prepare linear and branched polyorganosiloxanes with azidopropyl functions at the silicon atom. The study demonstrates effective methods for introducing these groups and the possibility of postpolymerization functionalization under green conditions using click chemistry.
ACS APPLIED POLYMER MATERIALS
(2022)
Article
Chemistry, Physical
Sofia Caby, Lydia M. Bouchet, Juan E. Arguello, Roberto A. Rossi, Javier Bardagi
Summary: Both photochemical and electrochemical transformations offer opportunities for environmentally friendly methodologies, with potential for improvement if combined. The research compared pure photochemical and electro-photochemical transformations, identifying a system with potential applications in both approaches and recognizing the excitation of radical anion as a key event. Despite similar yields and reaction rates, differences exist in terms of setup simplicity, catalyst solubility tolerance, selectivity, and optimization possibilities between the two methods.
Article
Chemistry, Organic
Rebeca Martinez-Haya, Adrian A. Heredia, Willber D. Castro-Godoy, Luciana C. Schmidt, M. Luisa Marin, Juan E. Arguello
Summary: The study successfully combined transition-metal catalysis and photoredox catalysis to form the light-triggered CuAAC reaction. Depending on the choice of photocatalysts and additives, the reaction could have drastically different outcomes. Through experiments to determine reactivity and kinetic data, the proposed mechanisms were supported and the importance of kinetic studies in understanding photoredox processes was highlighted.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Nanoscience & Nanotechnology
Antonella Florencia Carrizo, Guilherme K. Belmonte, Fabiano S. Santos, Claudio W. Backes, Guilherme B. Strapasson, Luciana C. Schmidt, Fabiano S. Rodembusch, Daniel E. Weibel
Summary: The study demonstrates that polymer composite lead-halide perovskite nanocrystals (NCs) can achieve high fluorescence yield and complete water resistance, with PSU polymer playing a key role in enhancing the water stability of the fluorescent films.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Correction
Chemistry, Organic
Rebeca Martinez-Haya, Adrian A. Heredia, Willber D. Castro-Godoy, Luciana C. Schmidt, M. Luisa Marin, Juan E. Arguello
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Ignacio D. Lemir, Gabriela Oksdath-Mansilla, Willber D. Castro-Godoy, Luciana C. Schmidt, Juan E. Arguello
Summary: An eco-friendly photochemical method for the synthesis of sulfur and selenium compounds with high selectivity is reported. The use of continuous-flow systems reduces reaction time and improves product yields, making it relevant for the pharmaceutical industry.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2022)
Editorial Material
Chemistry, Organic
Miriam C. Strumia, Juan E. Arguello, Alejandro M. Fracaroli
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Editorial Material
Chemistry, Organic
Miriam Strumia, Juan E. Arguello, Alejandro M. Fracaroli
Article
Chemistry, Multidisciplinary
Willber D. Castro-Godoy, Lydia M. Bouchet, Marcelo Puiatti, Luciana C. Schmidt, Juan E. Arguello
Summary: This study demonstrates the reduction of substituted benzyl selenocyanates to diselenides using photoredox catalysis. The highest yields were achieved when Purpurin was used as the photocatalyst under LED irradiation and air atmosphere in the presence of triethylamine. The electrochemical properties of the studied compounds were also measured, revealing the ease of reduction of the Se-CN moiety.
Article
Chemistry, Organic
Adrian A. Heredia, Lydia M. Bouchet, Willber D. Castro-Godoy, Juan E. Arguello
Summary: Organoselenium chemistry has been successfully applied in biological, medicinal, and material sciences, but its application in organic synthesis is still in early stages. This review describes recent developments in electrochemistry and photochemistry for organoselenium synthesis, highlighting their environmentally sustainable properties and different approaches.
Article
Chemistry, Multidisciplinary
Daniel A. Caminos, Guido N. Rimondino, Eduardo Gatica, Walter A. Massad, Juan E. Arguello
Summary: The application of photocatalysis in organic synthesis depends on achieving good yields and ease of application. Selective irradiation of the photocatalyst with LED light enables easy activation of reactions without the need for UV or heat filters. However, separating the photocatalyst from the reaction products poses a challenge for recovery and reuse. Binding the photocatalyst to a heterogeneous support, such as chromatographic silica gel, allows for easy removal and reuse. The modified silica gel showed good photoactivity and size suitable for easy separation, paving the way for effective applications in photoinduced organic synthesis at medium to large scale.
Article
Chemistry, Multidisciplinary
Juan E. Argueello, Adrian A. Heredia, Lydia M. Bouchet
Summary: In this study, a variety of dye-sensitized TiO2 were prepared and used as a photocatalyst for the synthesis of phenols through the oxidative hydroxylation of boronic acids and esters. The combination of TiO2 with several organic dyes, including eosin Y, rose bengal, purpurin, alizarin blue, fluorescein, and riboflavin, was investigated, with TiO2-eosin Y showing the best results. The synergistic association between dyes and TiO2 was found to enhance its photocatalytic properties, and the reactions were successfully performed under heterogeneous photocatalytic conditions, yielding good to excellent isolated yields of the desired phenols.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2023)
