Carbonylation and Other Transformations of Polyfluorobenzocyclobutenols in Super Acids

S. Wang; Ван С.; Ya. V. Zonov; Зонов Я. В.; V. M. Karpov; Карпов В. М.; T. V. Mezhenkova; Меженкова Т. В.

doi:10.31857/S0514749224010031

Carbonylation and Other Transformations of Polyfluorobenzocyclobutenols in Super Acids

作者: Wang S.¹^,2, Zonov Y.V.¹^,2, Karpov V.M.¹, Mezhenkova T.V.¹
隶属关系:
1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences
2. Novosibirsk State University
期: 卷 60, 编号 1 (2024)
页面: 47-59
栏目: Articles
URL: https://clinpractice.ru/0514-7492/article/view/672218
DOI: https://doi.org/10.31857/S0514749224010031
EDN: https://elibrary.ru/ENSBKJ
ID: 672218

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Acid-catalyzed carbonylation of a number of polyfluorinated benzocyclobuten-1-ols, as well as cyclic sulfoesters of benzocyclobuten-1,2-diols, in reaction with carbon monoxide has been carried out. The efficiency of using TfOH and FSO₃H-SbF₅ as acidic systems was evaluated. Both products of CO addition with the remaining four-membered ring — the corresponding carboxylic acids, and various products of carbonylation accompanied by its transformations (ring opening, opening followed by heterocyclization with the formation of isochromane derivatives, expansion to a five-membered one) were obtained. In some cases, the formation of polycyclic dimeric products was also observed.

关键词

carbonylation, alcohols, carboxylic acids, polyfluorinated benzocyclobutenes, fluorosulfonic acid, trifluoromethanesulfonic acid, antimony pentafluoride

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Chambers R.D. Fluorine in Organic Chemistry. Oxford: Blackwell Publishing Ltd, 2004.
Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications. Weinheim: Wiley-VCH, 2004.
Политанская Л.В., Селиванова Г.А., Пантелеева Е.В., Третьяков Е.В., Платонов В.Е., Никульшин П.В., Виноградов А.С., Зонов Я.В., Карпов В.М., Меженкова Т.В., Васильев А.В., Колдобский А.Б., Шилова О.С., Морозова С.М., Бургарт Я.В., Щегольков Е.В., Салоутин В.И., Соколов В.Б., Аксиненко А.Ю., Ненайденко В.Г., Москалик М.Ю., Астахова В.В., Шаинян Б.А., Таболин А.А., Иоффе С.Л., Музалевский В.М., Баленкова Е.С., Шастин А.В., Тютюнов А.А., Бойко В.Э., Игумнов С.М., Дильман А.Д., Адонин Н.Ю., Бардин В.В., Масоуд С.М., Воробьева Д.В., Осипов С.Н., Носова Э.В., Липунова Г.Н., Чарушин В.Н., Прима Д.О., Макаров А.Г., Зибарев А.В., Трофимов Б.А., Собенина Л.Н., Беляева К.В., Сосновских В.Я., Обыденнов Д.Л., Усачев С.А. Усп. хим. 2019, 88, 425–569. [Politanskaya L.V., Selivanova G.A., Panteleeva E.V., Tretyakov E.V., Platonov V.E., Nikul’shin P.V., Vinogradov A.S., Zonov Ya.V., Karpov V.M., Mezhenkova T.V., Vasilyev A.V., Koldobskii A.B., Shilova O.S., Morozova S.M.,. Burgart Ya.V, Shchegolkov E.V., Saloutin V.I., Sokolov V.B., Aksinenko A.Yu., Nenajdenko V.G., Moskalik M.Yu., Astakhova V.V., Shainyan B.A., Tabolin A.A., Ioffe S.L., Muzalevskiy V.M., Balenkova E.S., Shastin A.V., Tyutyunov A.A., Boiko V.E., Igumnov S.M., Dilman A.D., Adonin N.Yu., Bardin V.V., Masoud S.M., Vorobyeva D.V., Osipov S.N., Nosova E.V., Lipunova G.N., Charushin V.N., Prima D.O., Makarov A.G., Zibarev A.V., Trofimov B.A., Sobenina L.N., Belyaeva K.V., Sosnovskikh V.Ya., Obydennov D.L., Usachev S.A. Russ. Chem. Rev. 2019, 88, 425–569.] doi: 10.1070/RCR4871
Organofluorine Chemistry: Principles and Commercial Applications, Eds. R.E. Banks, B.E. Smart, J.C.Tatlow, New York: Plenum, 1994.
Fluorine in medicinal chemistry and chemical biology. Ed. I. Ojima, Oxford: Wiley-Blackwell, 2009. 291–311.
Begue J.-P., Bonnet-Delpon D., Bioorganic and Medicinal chemistry of Fluorine, Wiley, Hoboken, 2008.
Tang M.L., Bao Z. Chem. Mater. 2011, 23, 446–455. doi: 10.1021/cm102182x
Babudri F., Farinola G.M., Naso F., Ragni R. Chem. Commun. 2007, 1003–1022. doi: 10.1039/B611336B
Purser S., Moore P.R., Swallow S., Gouverneur V. Chem. Soc. Rev. 2008, 37, 320–330. doi: 10.1039/b610213c
Zonov Ya.V., Karpov V.M., Platonov V.E. J. Fluor. Chem. 2014, 162, 71–77. doi 0.1016/j.jfluchem.2014.03.008
Zonov Ya.V., Karpov V.M., Mezhenkova T.V., Rybalova T.V., Yu.V. Gatilov, Platonov V.E. J. Fluor. Chem. 2016, 188, 117–125. doi: 10.1016/j.jfluchem.2016.06.014
Зонов Я.В., Карпов В.М., Меженкова Т.В. ЖОрХ. 2019, 55, 1193–1202. [Zonov Ya.V., Karpov V.M., Mezhenkova T.V. Russ. J. Org. Chem. 2019, 55, 1103–1111.] doi: 10.1134/S1070428019080086
Fu X.-F., Xiang Y. Yu, Z.-X. Chem. Eur. J. 2015, 21, 4242–4246. doi: 10.1002/chem.201405712
Чуйков И.П., Карпов В.М., Платонов В.Е. Изв. АН СССР. Сер. хим. 1992, 1412–1419. [Chuikov I. P., Karpov V.M., Platonov V.E. Bull. Acad. Sci. USSR. Div. Chem. Sci. 1991, 41, 1104–1110.] doi: 10.1007/BF00866597
Karpov V.M., Mezhenkova T.V., Platonov V.E., Sinyakov V.R. J. Fluor. Chem. 2002, 117, 73–81. doi: 10.1016/S0022-1139(02)00196-3
Зонов Я.В., Меженкова Т.В., Карпов В.М., Платонов В.Е. ЖОрХ. 2008, 44, 1675–1679. [Zonov Ya.V., Mezhenkova T.V., Karpov V.M., Platonov V.E. Russ. J. Org. Chem. 2008, 44, 1652−1656.] doi: 10.1134/S107042800811016X
Карпов В.М., Меженкова Т.В., Платонов В.Е., Синяков В.Р., Щеголева Л.Н. ЖОрХ. 2002, 38, 1210–1217. [Karpov V.M, Mezhenkova T.V, Platonov V.E., Sinyakov V.R., Shchegoleva L.N. Russ. J. Org. Chem. 2002, 38, 1158–1165.] doi: 10.1023/A:1020901526459
Ван С., Голохвастова Д.С., Зонов Я.В., Карпов В.М., Меженкова Т.В., Гатилов Ю.В. ЖОрХ. 2022, 58, 619–631. [Wang S., Golokhvastova D.S., Zonov Ya.V., Karpov V.M., Mezhenkova T.V., Gatilov Yu.V. Russ. J. Org. Chem. 2022, 58, 780–790.] doi: 10.31857/S0514749222060040
Зонов Я.В., Голохвастова Д.С., Карпов В.М., Меженкова Т.В. ЖОрХ. 2023, 59, 51–61. [Zonov Ya.V., Golokhvastova D.S., Karpov V.M., Mezhenkova T.V. Russ. J. Org. Chem. 2023, 59, 29–37.] doi: 10.1134/S1070428023010025