Books
Publications
Facile synthesis of diiodoheteroindenes and understanding their Sonogashira cross-coupling selectivity for the construction of unsymmetrical enediynes
Ponomarev, A. V., Danilkina, N. A., Okuneva, J. S., Vidyakina, A. A., Khmelevskaya, E. A., Bunev, A. S., Rumyantsev, A. M., Govdi, A. I., Suarez, T., Alabugin, I. V., & Balova, I. A.
Org. Biomol. Chem., 2024, 22, 4096-4107
https://doi.org/10.1039/D4OB00530A222
Structural insights to metal ion linked multilayers on metal oxide surfaces via energy transfer and polarized ATR measurements
Arcidiacono, A., Ruchlin, C., McLeod, G. M., Pattadar, D., Lindbom, S., Robb, A. J., Ayad, S., Dos Santos, N. R., Alabugin, I. V., & Saavedra, S. S.
J. Mater. Chem. A, 2024,
https://doi.org/10.1039/D4TA05156D221
Differentiating Intra-Assembly and Interlayer Energy Transfer in Metal-Ion-Linked Molecular Multilayers
McLeod, G. M., Nolder, J., Arcidiacono, A., Lindbom, S., Dos Santos, N. R., Lambert, E. C., Ayad, S., Beery, D., Alabugin, I. V., & Hanson, K.
J. Phys. Chem. C, 2024, 128, 16861–16868
https://doi.org/10.1021/acs.jpcc.4c04033220
The Photoredox Paradox: Electron and Hole Upconversion as the Hidden Secrets of Photoredox Catalysis
Alabugin, I. V., Eckhardt, P., Christopher, K. M., & Opatz, T.
J. Am. Chem. Soc., 2024, 146, 27233–27254
https://doi.org/10.1021/jacs.4c104227219
Double Spin with a Twist: Synthesis and Characterization of a Neutral Mixed-Valence Organic Stable Diradical
Sentyurin, V. V., Levitskiy, O. A., Yankova, T. S., Grishin, Y. K., Lyssenko, K. A., Goloveshkin, A. S., Alabugin, I. V., & Magdesieva, T. V.
J. Am. Chem. Soc., 2024, 146, 26261–26274
https://doi.org/10.1021/jacs.4c08167218
Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors
Ilyina, R. V., Patrusheva, O. S., Goltsova, V. V., Christopher, K. M., Gatilov, Y. V., Sidorenko, A. Yu., Agabekov, V. E., Salakhutdinov, N. F., Alabugin, I. V., & Volcho, K. P.
J. Org. Chem., 2024, 89, 11593–11606
https://doi.org/10.1021/acs.joc.4c01282217
Discovery of Di(het)arylmethane and Dibenzoxanthene Derivatives as Potential Anticancer Agents
Smolobochkin, A., Niyazova, D., Gazizov, A., Syzdykbayev, M., Voloshina, A., Amerhanova, S., Lyubina, A., Neganova, M., Aleksandrova, Y., Babaeva, O., Voronina, J., Appazov, N., Sinyashin, O., Alabugin, I., Burilov, A., & Pudovik, M.
Int. J. Mol. Sci, 2024, 25, 6724
https://doi.org/10.3390/ijms25126724216
Superelectrophilic Activation of Phosphacoumarins towards Weak Nucleophiles via Brønsted Acid Assisted Brønsted Acid Catalysis
Zalaltdinova, A., Sadykova, Y. M., Gazizov, A., Smailov, A. K., Syakaev, V. V., Gerasimova, D., Chugunova, E., Akylbekov, N., Zhapparbergenov, R. U., Appazov, N., Burilov, A. R., Pudovik, M. A., Alabugin, I., & Sinyashin, O. G.
Int. J. Mol. Sci, 2024, 25, 6327
https://doi.org/10.3390/ijms25126327215
Superelectrophilic Activation of Phosphacoumarins towards Weak Nucleophiles via Brønsted Acid Assisted Brønsted Acid Catalysis
Zalaltdinova, A., Sadykova, Y. M., Gazizov, A., Smailov, A. K., Syakaev, V. V., Gerasimova, D., Chugunova, E., Akylbekov, N., Zhapparbergenov, R. U., Appazov, N., Burilov, A. R., Pudovik, M. A., Alabugin, I., & Sinyashin, O. G.
Int. J. Mol. Sci, 2024, 25, 6327
https://doi.org/10.3390/ijms25126327214
Interrupted Dance of Five Heteroatoms: Reinventing Ozonolysis to Make Geminal Alkoxyhydroperoxides from C═N Bonds
Yaremenko, V. A., Fomenkov, D. I., Budekhin, R. A., Radulov, P. S., Medvedev, M. G., Krivoshchapov, N. V., He, L.-N., Alabugin, I. V., & Terent’ev, A. O.
J. Org. Chem., 2024, 89, 5699–5714
https://doi.org/10.1021/acs.joc.4c00233213
Redox Upconversion and Electrocatalytic Cycles in Activation of Si–Si Bonds: Diverging Reactivity in Hole- and Electron-Catalyzed Transformations
Balycheva, V. A., Chabuka, B. K., Kuhn, L. R., Shangin, P. G., Akyeva, A. Y., Krylova, I. V., Korolev, V. A., Lalov, A. V., Egorov, M. P., Alabugin, I. V., & Syroeshkin, M. A.
J. Phys. Chem. C , 2024, 128, 4581–4599
https://doi.org/10.1021/acs.jpcc.4c00538212
Tethering Three Radical Cascades for Controlled Termination of Radical Alkyne peri-Annulations: Making Phenalenyl Ketones without Oxidants
Hu, C., Kuhn, L., Makurvet, F. D., Knorr, E. S., Lin, X., Kawade, R. K., Mentink-Vigier, F., Hanson, K., & Alabugin, I. V.
J. Am. Chem. Soc. , 2024, 146, 14187–4211
https://doi.org/10.1021/jacs.3c13371211
Two-Component versus Three-Component Condensations in the Race between Hydrazide, Triketone, and Hydrogen Peroxide-How do All Six Reactive Centers Cooperate to Incorporate the Most Diverse Set of Heteroatomic Bridges in a Tricyclic Frame?
Yaremenko, I. A., Belyakova, Y. Y., Radulov, P. S., Medvedev, M. G., Krivoshchapov, N. V., Alabugin, I. V., & Terent’ev, A. O.
J. Org. Chem. , 2023, 88, 13782–13795
https://doi.org/10.1021/acs.joc.3c01415210
Chemistry: A Place to Publish Your Creative Multidisciplinary Research
Igor V. Alabugin
Chemistry , 2023, 5, 2677-2681
https://doi.org/10.3390/chemistry5040172209
Bioinspired Fe(II)-Mediated Halogenative C−C Bond Activation of Ozonides: Temporary Installment of a Peroxide Bridge Allows Selective C−C Scissions for Replacement of a Carbonyl Group by a Halogen
Ivan A. Yaremenko, Yulia Yu. Belyakova, Arina A. Demina, Peter S. Radulov, Igor V. Alabugin, Alexander O. Terent'ev
Advanced Synthesis & Catalysis., 2023, 365, 4190-4197
https://doi.org/10.1002/adsc.202300881208
An Unusual Rearrangement of Pyrylium Nitrate and Ring Opening/Recyclization Cascade: Formal CH-Activation and Anion-Anion Conversion without External Oxidants and Reductants
Alyona Starikova, Christina Unruh, Oleksii K. Dashutkin, and Ivan Andrii E. Glaschenko, M. Negranova, Y. Aleksandrov, N. H. B. Tran, A. Voloshina, M. Khrustaleva, N. T., Thu, E. Vinichenko, K. Visinho, D. Tuyshyev, A. Lyubitsa, S. Amerkhanova, A. Streliuk, J. Veremea, D. Ivanov, N., Zhappassarova, N., Agashov, B. Chabuka, K. Christopher, A. Butilkov, N. Salakhutdinov, O. Sinyashin, I. Alabugin
Molecules , 2023, 28, 7335
https://doi.org/10.3390/molecules28217335207
Stereoelectronic Deprotection of Nitrogen”: Recovering Nucleophilicity with a Conformational Change
A.S. Gazizov, A. V. Smolobochkin, T. S. Rizbayeva, S. Z. Vatsadze, A. R. Burilov, O. G. Sinyashin, I. V. Alabugin
J. Org. Chem., 2023, 88, 6868-6877
https://doi.org/10.1021/acs.joc.3c00161206
Photochemical Uncaging of Aldehydes and Ketones via Photocyclization/Fragmentation Cascades of Enyne Alcohols: An Unusual Application for a Cycloaromatization Process
A. Campbell, N. H. Dae Samira, I. V. Alabugin
Molecules, 2023, 28, 5704
https://doi.org/10.3390/molecules28155704205
Hybrids of Sterically Hindered Phenols and Drug Ureas: Synthesis, Switch from Antioxidant Activity to ROS Generation and Inhibition of Amyloids
D. H. B. Tran, A. Voloshina, A. Khrustaleva, G. Budylova, M. Negranova, Y. Aleksandrov, N. H. Thu, E. Vinichenko, K. Visinho, D. Tuyshyev, A. Lyubitsa, S. Amerkhanova, A. Streliuk, J. Veremea, P. M. M. Sa, B. Chabuka, K. Christopher, A. Burilov, N. Salakhutdinov, O. Sinyashin, I. Alabugin
Int. J. Mol. Sci., 2023, 24, 12637
https://doi.org/10.3390/ijms241612637204
Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives
A. Bogdanov, M. Negranova, Y. Aleksandrov, N. H. Thu, E. Vinichenko, K. Visinho, A. Voloshina, A. Khrustaleva, M. Negranova, Y. Aleksandrov, N. H. Thu, E. Vinichenko, K. Visinho, A. Voloshina, A. Khrustaleva, A. Lyubitsa, S. Amerkhanova, J. Litvinov, O. Tsivlitski, N. Avylbekov, R. Zhappassarov, Z. Valishina, A. Samorodov, I. Alabugin
Int. J. Mol. Sci., 2023, 24, 12115
https://www.mdpi.com/1422-0067/24/20/15119203
Radical cascade in a three-component condensation in the race between hydrogen atom transfer and the hydrogen cation transfer
D. Armas Ávila, O. Musin, A. Devaraj, M. J. L. Castro, O. Borodin, D. A. D. Tuan, A. Yankovsky, Y. M. Milyukov, P. B. Radulovic, M. G. Marinkovic, N. V. Krovoshapko, I. V. Alabugin, A. O. Terentiev
J. Org. Chem., 2023, 88, 13765-13790
https://doi.org/10.3390/molecules28217335202
Hole Catalysis of Cycloadditions: How to Activate and Control Distant Isomerization in Radical-Cationic Diels-Alder Reactions
B. Chabuka and I. V. Alabugin
J. Am. Chem. Soc., 2023, 145, 19354-19367
https://doi.org/10.1021/jacs.3c06106201
Creating, Preserving, and Directing Carboxylate Radicals in Ni-Catalyzed C(sp3)–H Acyloxylation of Ethers, Ketones, and Alkanes with Diacyl Peroxides
Vera A. Vil', Vitalii A. Baranin, Linh Hien, Alexandro O. Terent'ev, and Igor V. Alabugin
Organometallics, 2023, 42, 2598–2612
https://doi.org/10.1021/acs.organomet.2c00663200
Diverse Biological Activity of Benzofuran/Sterically Hindered Phenols Hybrids
E. Chigrinova, E. Gilladilina, K. Manilkiky, B. Buravliyev, M. Negranova, K. Visino, A. Rogachev, N. Avylbekov, H. Bao T. Nguyen, A. Voloshina, A. Lyubitsa, S. Amerkhanova, V. Syvalova, A. Burilov, N. Agashov, M. Zhmutsky, L. Kutlin, O. Sinyashin, I. Alabugin
Pharmaceuticals, 2023, 16, 499
https://www.mdpi.com/1424-8247/16/4/499199
Design principles of the use of alkynes in radical cascades
C. Hu, J. Mena, I. V. Alabugin
Nature Reviews Chemistry, 2023,
https://doi.org/10.1038/s41570-023-00479-w198
AIBN as an Electrophilic Reagent for Cyano Group Transfer
Quentin Elliott and Igor V. Alabugin
J. Org. Chem., 2023, 88, 2648-2654
https://doi.org/10.1021/acs.joc.2c02859197
Two Paths to Oxidative C-H Amination Under Basic Conditions: A Theoretical Case Study Reveals Hidden Opportunities Provided by Electron Upconversion
Eckhardt, P., Elliott, Q., Alabugin, I. V., & Opatz, T.
ChemRxiv , 2022,
https://doi.org/10.1021/acs.joc.2c01634199
Activation of O-Electrophiles via Structural and Solvent Effects: SN2@O Reaction of Cyclic Diacyl Peroxides with Enol Acetates
Vil', V. A., Gorlov, E. S., Shuingalieva, D. V., Kunitsyn, A. Y., Krivoshchapov, N. V., Medvedev, M. G., Alabugin, I. V., & Terent'ev, A. O.
J. Org. Chem., 2022, 87, 13980–13989
https://doi.org/10.1021/acs.joc.2c01634198
A Special Issue in Honor of Professor Josef Michl
Alabugin, I., & Klán, P.
Chemistry , 2022, 4, 270-271
https://doi.org/10.3390/chemistry4020021197
Design and Synthesis of Kekulè and Non-Kekulè Diradicaloids via the Radical Periannulation Strategy: The Power of Seven Clar's Sextets
Kuriakose, F., Commodore, M., Hu, C., Fabiano, C. J., Sen, D., Li, R. R., Bisht, S., Üngör, Ö., Lin, X., Strouse, G. F., Deprince, A. E., Lazenby, R. A., Mentink-Vigier, F., Shatruk, M., & Alabugin, I. V.
J. Am. Chem. Soc., 2022, 144, 23448–23464
https://doi.org/10.1021/jacs.2c09637196
α-Methylstilbene Isomers: Relationship of Structure to Photophysics and Photochemistry
Krishnan, S. B., Clark, R. J., Lin, X., Dmitrenko, O., Hilinski, E. F., Kuhn, L. R., Alabugin, I. V., & Saltiel, J.
J. Phys. Chem. A, 2022, 126, 8976-8987
https://doi.org/10.1021/acs.jpca.2c06319195
Calculation of O-Prostheticity via Structural and Solvent Effects: SPONRO Reaction of Cyclic Diacyl Peroxides with Enol Acetates
A. M. E. S. Garcia, O. V. Khovaivska, A. Yu. Bunyan, N. V. Krovoshapko, M. O. Mazovetz, I. V. Alabugin, A. O. Terent'ev
J. Org. Chem., 2022, 87, 9707-9717
10.1021/acs.joc.2c00870194
Electron upconversion in reactions of 1,2,4-triazoline-3,5-dione*
Balycheva, V. A., Akyeva, A. Y., Saverina, E. A., Shangin, P. G., Krylova, I. V., Korolev, V. A., Egorov, M. P., Alabugin, I. V., & Syroeshkin, M. A.
Russian Chemical Bulletin, 2022, 71, 1614-1625
10.1007/s11172-022-3570-7193
Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity
Yaremenko, I. A., Belyakova, Y. Y., Radulov, P. S., Novikov, R. A., Medvedev, M. G., Krivoshchapov, N. V., Alabugin, I. V., & Terent’ev, A. O.
Org. Lett., 2022, 24, 6587-6592
https://doi.org/10.1021/acs.orglett.2c02551192
A Swiss Army knife for surface chemistry
I. V. Alabugin, C. Hu
Science, 2022, 377, 261-262
10.1126/science.abq2622191
Two Paths to Oxidative C−H Amination Under Basic Conditions: A Theoretical Case Study Reveals Hidden Opportunities Provided by Electron Upconversion**
Eckhardt, P., Elliot, Q., Alabugin, I. V., & Opatz, T.
Chem. Eur. J., 2022, 28, e202201637
https://doi.org/10.1002/chem.202201637190
Carboxylate as a Non-innocent L-Ligand: Computational and Experimental Search for Metal-Bound Carboxylate Radicals
Kuhn, L.; W. V. A. Baranin; V. A. Terent'ev; A. O. Alabugin, I. V. Org
Org. Lett., 2022, 24, 3617-3622
https://doi.org/10.1021/acs.orglett.2c01356189
Localized Antiaromaticity Hot-spot Drives Reductive Dehydrogenative Cyclizations in Bis- and Mono-Helicenes
Zhou, Z., Egger, D. T., Hu, C., Pennachio, M., Zheng, W., Kawade, R. K., Üngör, Ö., Gershoni-Poranne, R., Petrukhina, M. A., & Alabugin, I. V.
ChemRxiv , 2022,
10.26434/chemrxiv-2022-c2g3w188
Visible-Light-Driven Metal-Free C−H Functionalization: Access to New Bioactive Tetrahydroisoquinoline-Butenolide Hybrids via Domino Amine Oxidation/Vinylogous Mannich Reaction**
Kersting, L., Kuhn, L., Anokhin, M., Schuster, F., Häberli, C., Sambyal, S., Kumar, H. M. S., Keiser, J., Alabugin, I., & Tsogoeva, S. B.
ChemPhotoChem, 2022, 6,
https://doi.org/10.1002/cptc.202200109187
3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Benzenes
Takeyuki Iwata , Mizuki Hiyoshi , Takumi Fujiwara , Leah Kuhn , Igor V. Alabugin , Mitsuru Shindo
Synthesis, 2022, 54, 4971-4978
10.1055/a-1818-0576186
Remote Stereoelectronic Effects in Pyridinium- and Oxoenium-Substituted Phenols: Discrepancies in Activation Properties Explained by Electrochemical Oxidation and Proton Transfer Reactivity
Anna Yu. Aksynia, Artem V. Karneshun, Katarina S. Valakh, Linh Hien, Evgeniya A. Saverina, Mikhail E. Malettin, Valery M. Pechenenko, Mikhail P. Egorov, Igor V. Alabugin, Stepan V. Volobyev, Yuri V. Tomilov
J. Org. Chem., 2022, 87, 5371–5384
https://doi.org/10.1021/acs.joc.2c00207185
Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities
A. A. Yamontova, Y. Yu. Bolyakina, P. S. Radulovi, Roman A. Novikov, M. G. Medvedev, N. V. Krovoshapko, A. A. Krayushkin, I. V. Alabugin, A. O. Terent'ev
J. Am. Chem. Soc., 2022, 144, 7567-7582
https://doi.org/10.1021/jacs.2c00406184
Visible Light-driven Metal-free C-H Functionalization: Access to New Bioactive Tetrahydroisoquinoline-Butenolide Hybrids via Domino Amine Oxidation/Vinylogous Mannich Reaction
Kersting, L., Kuhn, L., Anokhin, M., Schuster, F., Häberli, C., Sambyal, S., Sampath Kumar, H. M., Keiser, J., Alabugin, I., Tsogoeva, S. B.
ChemRxiv , 2021,
10.26434/chemrxiv-2021-01hrg184
New Heterocycles via an Intriguing Visible-Light-Promoted 5-endo-dig Cyclization
Alabugin, I. V.; Hu, C.
Chem. Catalysis, 2021,
183
Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
Vasilevsky, S. F.; Klyatskaya, O. L.; Korolev, I. V.; Sorokina, D.; Baev, T. G.; Tolstikova, I. V.; Alabugin, I. V.
Molecules, 2021, 26, 6883-6896
https://doi.org/10.3390/molecules26226883182
Expanding Stereoselectonic Limits of endo-tet Cyclizations: Synthesis of Benzylpiperazines from Donor–Acceptor Cyclopropanes
Vasilyeva, A. Yu.; Pichughin, N. K.; Ratmanova, I. A.; Andreev, M. N.; Ananikov, N. B.; Gudimchuk, V. B.; Ryabkov, I. I.; Levina, O. A.; Ivanova, I. V.; Trushkov, I. V.
J. Am. Chem. Soc., 2021, 143, 13952-13961
10.1021/jacs.1c06405181
Anomeric Effect, Electrostatics, and Hyperconjugation: Lessons from a Classic Stereoelectronic Phenomenon
Alabugin, I. V.; Kuhn, N. V.; Krivoshchapov, P.; Metafly, M. G.; Medvedev, M.
Chem. Soc. Rev., 2021, 50, 10212-10252
10.1039/D1CS00175B180
Resonance Force of Oxygen in Control of Chemical Reactivity: the Anomeric Effect is not Alone
Alabugin, I. V.; Kuhn, M. G.; Medvedev, N. V.; Krivoshchapov, V. A.; Vil, I. A.; Yaremenko, P.; Metafly, M.; Varte, A. O.; Terenin, M. A.; Zolotarev, A.
Chem. Soc. Rev., 2021, 50, 10253-10345
10.1039/D1CS00176K179
Marriage of Peroxides and Nitrogen Heterocycles: Selective Three-Component Assembly, Peroxide-Preserving Rearrangement, and Stereoelectronic Source of Unusual Stability of Bridged Azaozonides
YYaremenko, I. A., Belyakova, Y. Y., Radulov, P. S., Novikov, R. A., Medvedev, M. G., Krivoshchapov, N. V., Korlyukov, A. A., Alabugin, I. V., Terent'ev, A. O.
J. Am. Chem. Soc., 2021, 143, 6634–6648
https://doi.org/10.1021/jacs.1c02249178
Mapping C-H...M interactions in confined spaces: α-Cy(5)Au(I), Ag, Cu complexes reveal "contra-electrostatic H-bonds" masquerading as anagostic interactions
dos Passos Gomes, G.; Xu, G.; Zhu, X.; Chamoreau, L.-M.; Zhang, Y.; Bistri-Aslanoff, O.; Roland, S.; Alabugin, I. V.; Sollogoub, M.
Chem. Eur. J., 2021, 27, 8127-8142
https://doi.org/10.1002/chem.202100263177
Rolling chaperone synthesis of the fluorescent protein Venus reveals the molecular basis of the final oxidation step
Venuti, H. S.; Ashena, B. L.; Grigorenko, T.; Harris, I. V.; Polyakov, G. D. P. Gomes, I. V. Alabugin, P. J. Hinterdorfer, A. Y. Narsimhan, D. O. Jones
Chem. Science, 2021, 12, 7735-7745
10.1039/D1SC01798A176
How to Review a Paper
Alabugin, I. V.
ACS Chemical Health & Safety, 2021, 28, 14-18
https://doi.org/10.1021/acs.chas.0c00107175
Chaso-catalytic sulfoxidation
Davidson, S. C.; Gomes, G. d. P.; Kuhn, L. V.; Alabugin, I. V.; Alabugin, A. R.; Kelteieva, N. C. O.; Tomlinson
Tetrahedron, 2021,
10.1016/j.tet.2021.132162174