Article
Chemistry, Multidisciplinary
Yu G. Borisova, Sh Sh Dzhumaev, N. S. Khusnutdinova, L. M. Mryasova, G. Z. Raskildina, S. S. Zlotskii
Summary: The study involved synthesizing new compounds and investigating their herbicidal activity, confirming the feasibility and prospects of herbicides containing cycloacetal and gem-dichlorocyclopropane fragments in their structure.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Songlin Yan, Weijie Yu, Jianye Zhang, Hongmei Fan, Zhifeng Lu, Zhenming Zhang, Tao Wang
Summary: An organic photoredox-catalyzed gem-difluoroallylation of alpha-trifluoromethyl alkenes with alkyl iodides via C-F bond cleavage for the synthesis of gem-difluoroalkene derivatives is reported. The transition-metal-free transformation utilized a readily available organic dye as the sole photocatalyst and provided good to high yields with a variety of iodides, including primary, secondary, and tertiary alkyl iodides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ren-Yin Yang, Hui Wang, Bo Xu
Summary: A new synthesis method has been developed to prepare gem-difluoroalkenes from readily available alkyl triflones and difluorocarbene precursors, yielding good to excellent product yields regardless of electronic effects. The mechanism likely involves deprotonation of triflones, nucleophilic addition, and the elimination of SO2CF3.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yuanqiang Guo, Yunpeng Cao, Hongjian Song, Yuxiu Liu, Qingmin Wang
Summary: A new example of relay catalysis using a combination of Mn-2(CO)(10) and an iridium-based photocatalyst has been reported. The Mn catalyst and iridium-based photocatalyst catalyze the reaction at different stages in the desired sequence under the same reaction conditions, transforming alkyl iodides into gem-difluoroalkenes with good functional group tolerance. This convenient method is suitable for late-stage modification of multifunctional complex molecules.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yin Liu, Pengfei Li, Jun Tan, Guangsheng Kou, Dengke Ma, Youai Qiu
Summary: In this article, a direct and efficient electrochemical method for synthesizing monofluoroalkene products using gem-difluoroalkenes and unactivated alkyl halides was described. The mechanism involving an alkyl radical intermediate was proposed based on detailed mechanistic studies. The advantages of electrochemistry, broad substrate scope, excellent functional group tolerance, and good Z-selectivity make this method environmentally friendly and economically feasible, with potential applications in organic synthesis and drug discovery.
Article
Chemistry, Organic
Jie Shi, Li-Yun Guo, Qu-Ping Hu, Yu-Tao Liu, Qing Li, Fei Pan
Summary: A photoredox-catalyzed radical cascade reaction has been developed for the synthesis of lactam-substituted gem-difluoroalkenes, providing a simple method with good functional group tolerance and high yields.
Review
Chemistry, Multidisciplinary
Qingjiang Li, Xiao-Bin Liu, Honggen Wang
Summary: This review systematically summarizes the recent development of iodine(III)-mediated migratory gem-difluorination reactions for the synthesis of gem-difluoroalkanes bearing a synthetically versatile functionality at the beta position, and discusses the reaction mechanism and the utilities of the products.
Article
Chemistry, Applied
Manman Wang, Mengyu Wu, Rui Ma, Kai Chen, Chuan Zhu, Chao Feng
Summary: A dehydrogenative fluorination method has been developed for the synthesis of multi-substituted trifluoromethylalkenes from various gem-difluoroalkenes using only electrophilic fluorination reagent NFSI. The reaction is tolerant to a wide range of functional groups, thereby complementing the existing synthetic protocols. Additionally, a visible-light-promoted stereoinversion strategy was discovered to obtain E-isomer enriched products.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Tamal Roy, Nadia N. Petersen, Greeshma Gopalan, Johan Gising, Mathias Hallberg, Mats Larhed
Summary: Ligands with a benzimidazole ring demonstrate high affinity and receptor selectivity. The substitution of bulky groups in the 2-position enhances these properties. The stability of ligands in human liver microsomes varies depending on the terminal group.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Cai-Yi Li, Yue Ma, Zhi-Wei Lei, Xiang-Guo Hu
Summary: A stereoselective, glycosyl radical-based method has been developed for the synthesis of C-alkyl glycosides via a photomediated defluorinative gem-difluoroallylation reaction. This method demonstrates the feasibility of glycosyl radicals participating in a photomediated radical polar crossover process, offering a diverse array of gemdifluoroalkene containing C-glycosides. Key features of this method include scalability, mild conditions, broad substrate scope, and suitability for late-stage modification of complex molecules.
Article
Chemistry, Applied
Vyacheslav I. Supranovich, Vitalij V. Levin, Vladimir A. Kokorekin, Alexander D. Dilman
Summary: Thiols react with alpha-(trifluoromethyl)styrenes under photocatalytic conditions, leading to desulfurative allylic fluorine substitution and formation of gem-difluorostyrenes.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Medicinal
Marco Robello, Hongchao Zheng, Mrinmoy Saha, Kara M. George Rosenker, Subrata Debnath, Jay Prakash Kumar, Harichandra D. Tagad, Sharlyn J. Mazur, Ettore Appella, Daniel H. Appella
Summary: In this study, a new molecular scaffold to inhibit Wip1 phosphatase was reported. Structure-activity relationships were examined by extensively modifying different portions of the core structure.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Karen de la Vega-Hernandez, Fabrice Chemla, Franck Ferreira, Olivier Jackowski, Alejandro Perez-Luna
Summary: The stereoselective germylzincation of internal alkynes delivering trisubstituted vinylgermanes is achieved via a radical chain process, showing excellent regiocontrol for nonsymmetric substrates. Additionally, the germylzincation reaction can be combined with the Cu(I)-mediated electrophilic substitution of the C(sp(2))-Zn bond to obtain synthetically challenging tetrasubstituted vinylgermanes.
Article
Chemistry, Applied
Ian W. Ashworth, Debasis Dey, Olivier Dirat, Paul McDaid, Daniel Lee, Justin Moser, Kausik K. Nanda
Summary: The presence of low levels of N-nitrosamines in active pharmaceutical intermediates and active ingredients is a topic of concern for industry and regulatory authorities. Experimental data suggests that the current kinetic model of dialkylamine nitrosation may overpredict the formation of N-nitrosamines. Furthermore, research shows that trialkylamines undergo nitrosative dealkylation to form N-nitrosamines, but at a significantly lower rate compared to dialkylamines.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
Article
Chemistry, Multidisciplinary
Yunxiao Zhang, Yunhong Niu, Youyuan Guo, Jiaxin Wang, Yizhi Zhang, Shanshan Liu, Xiao Shen
Summary: In this study, photocatalyzed cascade reactions between readily available cyclopropanols and alpha-trifluoromethyl-substituted olefins were reported for the synthesis of fused gem-difluorooxetanes. Two rings and three bonds were efficiently constructed in one reaction. The reaction demonstrated broad substrate scope and the downstream transformations of the products highlighted the synthetic potential. Mechanistic study supported the presence of cascade photoredox catalysis and energy transfer catalysis/direct photo-excitation processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Elena K. Beloglazkina, Olga O. Krasnovskaya, Dmitry A. Guk, Viktor A. Tafeenko, Anna A. Moiseeva, Nikolai Zyk, Alexander G. Majouga
Article
Chemistry, Multidisciplinary
A. A. Beloglazkina, D. A. Skvortsov, V. A. Tafeenko, A. G. Majouga, N. V. Zyk, E. K. Beloglazkina
RUSSIAN CHEMICAL BULLETIN
(2018)
Article
Chemistry, Multidisciplinary
O. B. Bondarenko, A. I. Komarov, L. I. Kuznetsova, S. N. Nikolaeva, A. Yu. Gavrilova, N. V. Zyk
RUSSIAN CHEMICAL BULLETIN
(2018)
Review
Chemistry, Organic
A. I. Konovalov, I. S. Antipin, V. A. Burilov, T. I. Madzhidov, A. R. Kurbangalieva, A. V. Nemtarev, S. E. Solovieva, I. I. Stoikov, V. A. Mamedov, L. Ya. Zakharova, E. L. Gavrilova, O. G. Sinyashin, I. A. Balova, A. V. Vasilyev, I. G. Zenkevich, M. Yu. Krasavin, M. A. Kuznetsov, A. P. Molchanov, M. S. Novikov, V. A. Nikolaev, L. L. Rodina, A. F. Khlebnikov, I. P. Beletskaya, S. Z. Vatsadze, S. P. Gromov, N. V. Zyk, A. T. Lebedev, D. A. Lemenovskii, V. S. Petrosyan, V. G. Nenaidenko, V. V. Negrebetskii, Yu. I. Baukov, T. A. Shmigol, A. A. Korlyukov, A. S. Tikhomirovg, A. E. Shchekotikhing, V. F. Traven, L. G. Voskresenskii, F. I. Zubkov, O. A. Golubchikov, A. S. Semeikin, D. B. Berezin, P. A. Stuzhin, V. D. Filimonov, E. A. Krasnokutskaya, A. Yu. Fedorov, A. V. Nyuchev, V. Yu. Orlov, R. S. Begunov, A. I. Rusakov, A. V. Kolobov, E. R. Kofanov, O. V. Fedotova, A. Yu. Egorova, V. N. Charushin, O. N. Chupakhin, Yu. N. Klimochkin, V. A. Osyanin, A. N. Reznikov, A. S. Fisyuk, G. P. Sagitullina, A. V. Aksenov, N. A. Aksenov, M. K. Grachev, V. I. Maslennikova, M. P. Koroteev, A. K. Brel, S. V. Lisina, S. M. Medvedeva, Kh. S. Shikhaliev, G. A. Suboch, M. S. Tovbis, L. M. Mironovich, S. M. Ivanov, S. V. Kurbatov, M. E. Kletskii, O. N. Burov, K. I. Kobrakov, D. N. Kuznetsov
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Inorganic & Nuclear
Elena K. Beloglazkina, Anna V. Yudina, Egor A. Pasanaev, Irina A. Salimova, Viktor A. Tafeenko, Andrei V. Mironov, Anna A. Moiseeva, Vladimir I. Pergushov, Nikolai V. Zyk, Alexander G. Majouga
INORGANIC CHEMISTRY COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Oksana B. Bondarenko, Aleksandr A. Vinogradov, Arseniy I. Komarov, Georgy L. Karetnikov, Nikolai V. Zyk, Tina Holt, Andrei G. Kutateladze
Article
Chemistry, Multidisciplinary
O. B. Bondarenko, A. Komarov, G. L. Karetnikov, S. N. Nikolaeva, N. Zyk
RUSSIAN CHEMICAL BULLETIN
(2019)
Article
Chemistry, Multidisciplinary
Oksana B. Bondarenko, Zaur M. Garaev, Arseniy I. Komarov, Lyubov I. Kuznetsova, Svetlana V. Gutorova, Dmitry A. Skvortsov, Nikolai V. Zyk
MENDELEEV COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Oksana B. Bondarenko, Arseniy I. Komarov, George L. Karetnikov, Svetlana N. Nikolaeva, Nikolai V. Zyk, Tina Holt, Andrei G. Kutateladze
Article
Chemistry, Organic
Oksana B. Bondarenko, Nikolai V. Zyk
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2020)
Article
Chemistry, Organic
A. Yu Gavrilova, O. B. Bondarenko, V. N. Tikhanushkina, T. A. Solodovnikova, N. Zyk
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Oksana B. Bondarenko, Nikolai V. Zyk
Summary: The review discusses methods for synthesizing haloisoxazoles and their applications in modern organic synthesis and medicinal chemistry, with a bibliography of 92 literature sources.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2020)
Article
Chemistry, Organic
Oksana B. Bondarenko, Georgy L. Karetnikov, Arseniy Komarov, Aleksandr Pavlov, Svetlana N. Nikolaeva
Summary: A new halogenating system has been proposed for the straightforward synthesis of halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles, and electron-rich benzenes, with excellent regioselectivity, scalability, and broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol has been developed for the efficient synthesis of 3,5-diaryl-4-haloisoxazoles from 1,2-diarylcyclopropanes under the suggested nitrosating-halogenating conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Georgy L. Karetnikov, Dmitry A. Skvortsov, Elena Lopatukhina, Svetlana N. Nikolaeva, Oksana B. Bondarenko
Summary: A novel two-stage regioselective synthesis method has been developed for the efficient preparation of non-symmetric 3,5-diarylisoxazoles, starting from readily available 2-aryl-1,1-dibromocyclopropanes. Using this strategy, a series of CA-4 analogues featuring a 3,5-diarylisoxazole motif were synthesized and evaluated for their biological activity, demonstrating promising results.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemical Research Methods
Oksana B. Bondarenko, Arseniy I. Komarov, Svetlana N. Nikolaeva, Tina Holt, Andrei G. Kutateladze, Igor P. Gloriozov
Summary: The fragmentation reaction of radical cations of 3-aryl-5-fluoroisoxazoles formed via EI-MS is described in this study. A new rearrangement accompanied by fluorine atom migration is discovered. A mechanistic rationale for the rearrangement, supporting the existence of a fluorinated benzocyclopropenyl cation, is proposed based on experimental data and quantum chemical calculations.
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2023)
