Аннотация:
This minireview describes chemistry of hypervalent organoiodine triflates, which have received wide synthetic application as powerful electrophilic reagents and oxidants. The first representative of these compounds, μ-oxo-bis[(trifluoromethanesulfonato)(phenyl)iodine], was originally prepared and investigated in N. S. Zefirov's laboratory at Moscow State University in the early 1980s. This compound, now commonly known as Zefirov's reagent, is a useful reagent for the synthesis of various iodonium salts from the corresponding organic precursors. Recently, thermally stable and highly reactive triflates derived from cyclic hypervalent iodine compounds, benziodoxoles, have been reported and utilized in organic synthesis. The strongest iodine(V) oxidant, IBX-ditriflate, has been prepared from 2-iodoxybenzoic acid (IBX) and triflic acid. IBX-ditriflate can readily oxidize organic substrates that are generally resistant to oxidation.
Образец цитирования:
M. S. Yusubov, V. V. Zhdankin, “Zefirov's reagent and related hypervalent iodine triflates”, Mendeleev Commun., 31:3 (2021), 282–287
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc906
https://www.mathnet.ru/rus/mendc/v31/i3/p282
Эта публикация цитируется в следующих 10 статьяx:
Akira Yoshimura, Viktor V. Zhdankin, “Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents”, Chem. Rev., 124:19 (2024), 11108
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
Lachlan Sharp-Bucknall, Marcus Sceney, Keith F. White, Jason L. Dutton, “Synthesis, structural characterization, reactivity and catalytic activity of mixed halo/triflate ArI(OTf)(X) species”, Dalton Trans., 52:11 (2023), 3358
Hui‐Cheng Cheng, Jiao‐Li Ma, Peng‐Hu Guo, “Cyclic Diaryliodonium Salts: Eco‐Friendly and Versatile Building Blocks for Organic Synthesis”, Adv Synth Catal, 365:8 (2023), 1112
Nasrin Ghanbari, Saeed Zakavi, “A hypervalent iodine secondary oxidant synthesized by photosensitized singlet oxygen: Synthesis, characterization and oxidative reactivity”, Journal of Catalysis, 405 (2022), 545
Lachlan Sharp‐Bucknall, Tania, Jason L. Dutton, “Synthesis and Structural Verification of an ArI(OTf)2, NO2‐Ph‐I(OTf)2**”, Angewandte Chemie, 134:46 (2022)
Antoine Juneau, Iannick Lepage, Sami G. Sabbah, Arthur H. Winter, Mathieu Frenette, “Mechanistic Insight into Phenol Dearomatization by Hypervalent Iodine: Direct Detection of a Phenoxenium Cation”, J. Org. Chem., 87:21 (2022), 14274
Anjali Dahiya, Ashish Kumar Sahoo, Nikita Chakraborty, Bubul Das, Bhisma K. Patel, “Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles”, Org. Biomol. Chem., 20:10 (2022), 2005
Lachlan Sharp‐Bucknall, Tania, Jason L. Dutton, “Synthesis and Structural Verification of an ArI(OTf)2, NO2‐Ph‐I(OTf)2**”, Angew Chem Int Ed, 61:46 (2022)
Akira Yoshimura, Christopher D. Huss, Akio Saito, Tsugio Kitamura, Viktor V. Zhdankin, “2-Iodosylbenzoic acid activated by trifluoromethanesulfonic anhydride: efficient oxidant and electrophilic reagent for preparation of iodonium salts”, New J. Chem., 45:36 (2021), 16434