Аннотация:
Due to the broad interest to cycloalkynes in metal-free click chemistry, we present a focused review summarizing current approaches to structural and electronic modifications of cycloalkynes. We illustrate how the combination of reactant destabilization and transition state stabilization can lead to the design of more reactive cycloalkynes that are, paradoxically, less strained. We discuss the concept of ring strain in cycloalkynes and show that increased ring strain does not always equate to increased click reactivity. We summarize direct and remote electronic effects that can be used to enhance click reactivity in cycloalkynes and show how inclusion of transition state stabilizing stereoelectronic effects is essential for the rational design of the cycloalkyne click reagents.
Образец цитирования:
T. M. Harris, I. V. Alabugin, “Strain and stereoelectronics in cycloalkyne click chemistry”, Mendeleev Commun., 29:3 (2019), 237–248
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc1484
https://www.mathnet.ru/rus/mendc/v29/i3/p237
Эта публикация цитируется в следующих 49 статьяx:
Susmita Biswas, Pradip Dey, Goutam Ghosh, “Polymeric microgels: Synthesis, and emerging biomedical applications”, Journal of Macromolecular Science, Part A, 2025, 1
Alexandra A. Vidyakina, Sergey A. Silonov, Anastasia I. Govdi, Alexander Yu. Ivanov, Ekaterina P. Podolskaya, Irina A. Balova, Stefan Bräse, Natalia A. Danilkina, “Key role of cycloalkyne nature in alkyne-dye reagents for enhanced specificity of intracellular imaging by bioorthogonal bioconjugation”, Org. Biomol. Chem., 22:37 (2024), 7637
Javier M. Hurst, Rinku Yadav, Parker T. Boeck, Ion Ghiviriga, ChristiAnna L. Brantley, Łukasz Dobrzycki, Adam S. Veige, “Snapshot of cyclooctyne ring-opening to a tethered alkylidene cyclic polymer catalyst”, Chem. Sci., 15:38 (2024), 15873
Dennis Svatunek, “Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions”, Top Curr Chem (Z), 382:2 (2024)
Sam Forshaw, Jeremy S. Parker, William T. Scott, Richard C. Knighton, Neelam Tiwari, Samson M. Oladeji, Andrew C. Stevens, Yean Ming Chew, Jami Reber, Guy J. Clarkson, Mohan K. Balasubramanian, Martin Wills, “Increasing the versatility of the biphenyl-fused-dioxacyclodecyne class of strained alkynes”, Org. Biomol. Chem., 22:3 (2024), 590
Igor V. Alabugin, Paul Eckhardt, Kimberley M. Christopher, Till Opatz, “The Photoredox Paradox: Electron and Hole Upconversion as the Hidden Secrets of Photoredox Catalysis”, J. Am. Chem. Soc., 146:40 (2024), 27233
Mehak, Gurleen Singh, Riddima Singh, Gurjaspreet Singh, Jigmat Stanzin, Harminder Singh, Gurpreet Kaur, Jandeep Singh, “Clicking in harmony: exploring the bio-orthogonal overlap in click chemistry”, RSC Adv., 14:11 (2024), 7383
Harrison E. Bruggeman, Rachel Lorson, Lilia J. Allen, Logan G. Jackson, Winston Gee, Brandon E. Haines, “A Computational Study of Gold(I)-Catalyzed Isomerization of Cyclooctyne: A Case Study on the Mechanism of C(sp3)–H Insertion by Cationic Gold Alkyne Complexes and Model Studies”, Organometallics, 43:18 (2024), 2147
Alistair J. Sterling, Russell C. Smith, Edward A. Anderson, Fernanda Duarte, “Beyond Strain Release: Delocalization-Enabled Organic Reactivity”, J. Org. Chem., 89:14 (2024), 9979
В. Н. Чарушин, Е. В. Вербицкий, О. Н. Чупахин, Д. В. Воробьева, П. С. Грибанов, С. Н. Осипов, А. В. Иванов, С. В. Мартыновская, Е. Ф. Сагитова, В. Д. Дяченко, И. В. Дяченко, С. Г. Кривоколыско, В. В. Доценко, А. В. Аксенов, Д. А. Аксенов, Н. А. Аксенов, А. А. Ларин, Л. Л. Ферштат, В. М. Музалевский, В. Г. Ненайденко, А. В. Гулевская, А. Ф. Пожарский, Е. А. Филатова, К. В. Беляева, Б. А. Трофимов, И. А. Балова, Н. А. Данилкина, А. И. Говди, А. С. Тихомиров, А. Е. Щекотихин, М. С. Новиков, Н. В. Ростовский, А. Ф. Хлебников, Ю. Н. Климочкин, М. В. Леонова, И. М. Ткаченко, В. А.-о. Мамедов, В. Л. Мамедова, Н. А. Жукова, В. Э. Семëнов, О. Г. Синяшин, О. В. Борщев, Ю. Н. Лупоносов, С. А. Пономаренко, А. С. Фисюк, А. С. Костюченко, В. Г. Илькин, Т. В. Березкина, В. А. Бакулев, А. С. Газизов, А. А. Загидуллин, А. А. Карасик, М. Е. Кукушкин, Е. К. Белоглазкина, Н. Е. Голанцов, А. А. Феста, Л. Г. Воскресенский, В. С. Мошкин, Е. М. Буев, В. Я. Сосновских, И. А. Миронова, П. С. Постников, В, “Успехи в химии гетероциклических соединений в 21 веке”, Усп. хим., 93:7 (2024), RCR5125 ; V. N. Charushin, E. V. Verbitskiy, O. N. Chupakhin, D. V. Vorobyeva, P. S. Gribanov, S. N. Osipov, A. V. Ivanov, S. V. Martynovskaya, E. F. Sagitova, V. D. Dyachenko, I. V. Dyachenko, S. G. Krivokolylsko, V. V. Dotsenko, A. V. Aksenov, D. A. Aksenov, N. A. Aksenov, A. A. Larin, L. L. Fershtat, V. M. Muzalevskiy, V. G. Nenajdenko, A. V. Gulevskaya, A. F. Pozharskii, E. A. Filatova, K. V. Belyaeva, B. A. Trofimov, I. A. Balova, N. A. Danilkina, A. I. Govdi, A. S. Tikhomirov, A. E. Shchekotikhin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, Yu. N. Klimochkin, M. V. Leonova, I. M. Tkachenko, V. A.-o. Mamedov, V. L. Mamedova, N. A. Zhukova, V. E. Semenov, O. G. Sinyashin, O. V. Borshchev, Yu. N. Luponosov, S. A. Ponomarenko, A. S. Fisyuk, A. S. Kostyuchenko, V. G. Ilkin, T. V. Beryozkina, V. A. Bakulev, A. S. Gazizov, A. A. Zagidullin, A. A. Karasik, M. E. Kukushkin, E. K. Beloglazkina, N. E. Golantsov, A. A. Festa, L. G. Voskresenskii, V. S. Moshkin, E. M. Buev, V. Ya. Sosnovskikh, I, “The chemistry of heterocycles in the 21st century”, Russian Chem. Reviews, 93:7 (2024), RCR5125
Aleksandra A. Vidyakina, Andrey A. Shtyrov, Mikhail N. Ryazantsev, Alexander F. Khlebnikov, Ilya E. Kolesnikov, Vladimir V. Sharoyko, Dar'ya V. Spiridonova, Irina A. Balova, Stefan Bräse, Natalia A. Danilkina, “Development of Fluorescent Isocoumarin‐Fused Oxacyclononyne – 1,2,3‐Triazole Pairs”, Chemistry A European J, 29:47 (2023)
Eshani Das, Mark Aldren M. Feliciano, Pavel Yamanushkin, Xinsong Lin, Brian Gold, “Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom”, Org. Biomol. Chem., 21:44 (2023), 8857
S. F Vasilevsky, A. A Stepanov, “Alkyl, aryl and hetaryl acetylenes - highly reactive multifunctional compounds (a review)”, Žurnal obŝej himii, 93:10 (2023), 1479
Michael J. Holzmann, Namrata Khanal, Pavel Yamanushkin, Brian Gold, “Remote Strain Activation in a Sulfate-Linked Dibenzocycloalkyne”, Org. Lett., 25:2 (2023), 309
T. E. Anderson, Dasan M. Thamattoor, David Lee Phillips, “Formation of 3-Oxa- and 3-Thiacyclohexyne from Ring Expansion of Heterocyclic Alkylidene Carbenes: A Mechanistic Study”, Org. Lett., 25:9 (2023), 1364
S. F. Vasilevsky, A. A. Stepanov, “Alkyl, Aryl, and Hetaryl Acetylenes: Highly Reactive Multifunctional Compounds (A Review)”, Russ J Gen Chem, 93:10 (2023), 2417
ACS In Focus, Oxygen: The Key to Stereoelectronic Control in Chemistry, 2023
Takayuki Iwata, Mizuki Hyodo, Takumi Fujiwara, Ryusei Kawano, Leah Kuhn, Igor V. Alabugin, Mitsuru Shindo, “3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes”, Synthesis, 54:22 (2022), 4971
T. Harris, I. V. Alabugin, Click Chemistry, 2022
Shintaro Takahashi, María Frutos, Antoine Baceiredo, David Madec, Nathalie Saffon‐Merceron, Vicenç Branchadell, Tsuyoshi Kato, “Synthesis, Characterization and Reactivity of a σ‐Donating Ni0‐Stabilized Silyliumylidene Ion”, Angew Chem Int Ed, 61:37 (2022)