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Books

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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/D4OB00530A

222

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/D4TA05156D

221

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.4c04033

220

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.4c104227

219

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.4c08167

218

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.4c01282

217

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/ijms25126724

216

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/ijms25126327

215

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/ijms25126327

214

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.4c00233

213

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.4c00538

212

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.3c13371

211

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.3c01415

210

Chemistry: A Place to Publish Your Creative Multidisciplinary Research

Igor V. Alabugin

Chemistry , 2023, 5, 2677-2681

https://doi.org/10.3390/chemistry5040172

209

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.202300881

208

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/molecules28217335

207

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.3c00161

206

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/molecules28155704

205

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/ijms241612637

204

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/1422-0067/24/20/15119

203

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/molecules28217335

202

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.3c06106

201

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.2c00663

200

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/1424-8247/16/4/499

199

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-w

198

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.2c02859

197

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.2c01634

199

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.2c01634

198

A Special Issue in Honor of Professor Josef Michl

Alabugin, I., & Klán, P.

Chemistry , 2022, 4, 270-271

https://doi.org/10.3390/chemistry4020021

197

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.2c09637

196

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.2c06319

195

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.2c00870

194

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/s11172-022-3570-7

193

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.2c02551

192

A Swiss Army knife for surface chemistry

I. V. Alabugin, C. Hu

Science, 2022, 377, 261-262

10.1126/science.abq2622

191

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.202201637

190

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.2c01356

189

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-c2g3w

188

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.202200109

187

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-1818-0576

186

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.2c00207

185

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.2c00406

184

, 2021,

186

, 2021,

185

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-2021-01hrg

184

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/molecules26226883

182

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.1c06405

181

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/D1CS00175B

180

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/D1CS00176K

179

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.1c02249

178

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.202100263

177

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/D1SC01798A

176

How to Review a Paper

Alabugin, I. V.

ACS Chemical Health & Safety, 2021, 28, 14-18

https://doi.org/10.1021/acs.chas.0c00107

175

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.2021.132162

174