Activation of Phenyl-N-(triflyl)imino-λ3-iodane by Metal Salts in Reactions with Alkenes

A. S. Ganin; Ганин Антон Сергеевич; I. A. Garagan; Гараган Иван Александрович; M. M. Sobyanina; Собянина Мария Михайловна; M. Y. Moskalik; Москалик Михаил Юрьевич

doi:10.31857/S0514749224090048

Activation of Phenyl-N-(triflyl)imino-λ3-iodane by Metal Salts in Reactions with Alkenes

Autores: Ganin A.S.¹, Garagan I.A.¹, Sobyanina M.M.¹, Moskalik M.Y.¹
Afiliações:
1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
Edição: Volume 60, Nº 9 (2024)
Páginas: 973-983
Seção: Articles
URL: https://aspvestnik.ru/0514-7492/article/view/681712
DOI: https://doi.org/10.31857/S0514749224090048
EDN: https://elibrary.ru/QNWGCG
ID: 681712

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The reactions of alkenes with phenyl-N-(triflyl)imino-λ³-iodane PhI=NTf 1 under different conditions were studied. Optimization of the reaction conditions of 1 with styrenes in the presence of copper (I) chloride leads to aziridine and bis(triflamidation) products in different ratios. The use, in the same reaction, of silver nitrate as a catalyzing additive leads to 1-phenyl-2-(triflamido)ethyl nitrate. Involvement of camphene as substrate and varying the catalyzing additive under oxidizing conditions can lead to isomeric acetamidines. The possible biological activity for the obtained compounds was evaluated.

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alkenes, imino-λ3-iodane, aziridine, amidines, oxidative addition

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Minakata S., Morino Y., Oderaotoshi Y., Komatsu M., Chem. Commun. 2006, том?. 3337–3339. doi: 10.1039/B606499J
Gao P., Wei Y., Heterocycl. Commun. 2013, 19, 113–119. doi: 10.1515/hc-2012-0179
Minakata S., Acc. Chem. Res. 2009, 42, 1172–1182. doi: 10.1021/ar900059r
Yoshimura A., Nemykin V.N., Zhdankin V.V. Chem. Eur. J., 2011, 17, 10538–10541. doi: 10.1002/chem.201102265
Kobayashi Y., Masakado S., Takemoto Y. Angew. Chem. Int. Ed. 2018, 57, 693–697. doi: 10.1002/anie.201710277
Conry R.R., Tipton A.A., Striejewske W.S., Erkizia E., Malwitz M.A., Caffaratti A., Natkin J.A. Organometallics. 2004, 23, 5210–5218. doi: 10.1021/om040098g
Gopalan G., Dhanya B.P., Saranya J., Reshmitha T.R., Baiju T.V., Meenu M.T., Nair M.S., Nisha P., Radhakrishnan K.V. Eur. J. Org. Chem. 2017, том?. 3072–3077. doi: 10.1002/ejoc.201700410
Wu X.-L., Xia J.-J., Wang G.-W. Org. Biomol. Chem. 2008, 6, 548–553. doi: 10.1039/B717333D
Wu X.-L., Wang G.-W. Tetrahedron. 2009, 65, 8802–8807. doi: 10.1016/j.tet.2009.08.069
Morino Y., Hidaka I., Oderaotoshi Y., Komatsu M., Minakata S. Tetrahedron. 2006, 62, 12247–12251. doi: 10.1016/j.tet.2006.10.003
Cai Y., Liu X., Li J., Chen W., Wang W., Lin L., Feng X. Chem. Eur. J. 2011, 17, 14916–14921. doi: 10.1002/chem.201102453
Knight J.G., Muldowney M.P. J. Synlett. 1995, 9, 949–951. doi: 10.1055/s-1995-5128
Wu Q., Hu J., Ren X., Zhou J. Chem. Eur. J. 2011, 17, 11553–11558. doi: 10.1002/chem.201101630
Shainyan B.A., Moskalik M.Y., Starke I., Schilde U., Tetrahedron. 2010, 66, 8383–8386. doi: 10.1016/j.tet.2010.08.070
Moskalik M.Yu., Shainyan B.A., Ushakov I.A., Sterkhova I.V., Astakhova V.V. Tetrahedron. 2020, 76, 131018. doi: 10.1016/j.tet.2020.131018
Ganin A.S., Moskalik M.Y., Garagan I.A., Astakhova V.V., Shainyan B.A., Molecules. 2022, 27, 6910. doi: 10.3390/molecules27206910
Evans D.A., Woerpel K.A., Hinman M.M., Faul M.M., J. Am. Chem. Soc. 1991, 113, 726–728. doi: 10.1021/ja00002a080
Evans D.A., Faul M.M., Bilodeau M.T., J. Org. Chem. 1991, 56, 6744–6746. doi: 10.1021/jo00024a008
Han H., Park S.B., Kim S.K., Chang S., J. Org. Chem. 2008, 73, 2862–2870. doi: 10.1021/jo800134j
Cui Y., He C., J. Am. Chem. Soc. 2003, 125, 16202–16203. doi: 10.1021/ja038668b
Baba, T., Takahashi, S., Kambara, Y., Yoshimura, A., Nemykin, V.N., Zhdankin, V.V., Saito, A., Adv. Synth. Cat. 2017, 359, 3860–3864. doi: 10.1002/adsc.201700934
Sunagawa S., Morisaki F., Baba T., Tsubouchi A., Yoshimura A., Miyamoto K., Uchiyama M., Saito A.,Org. Lett. 2022, 24, 5230–5234. doi: 10.1021/acs.orglett.2c02264
Ochiai M., Kaneaki T., Tada N., Miyamoto K., Chuman H., Shiro M., Hayashi S., Nakanishi W., J. Am. Chem. Soc. 2007, 129, 12938–12939. doi: 10.1021/ja075811i
Hoque M.M., Miyamoto K., Tada N., Shiro M., Ochiai M., Org. Lett. 2011, 13, 5428–5431. doi: 10.1021/ol201868n
Shainyan B.A., Moskalik M.Y., Astakhova V.V., Russ. J. Org. Chem. 2012, 48, 918–923. doi: 10.1134/S1070428012070056
Moskalik M.Y., Shainyan B.A., Schilde U., Russ. J. Org. Chem. 2011, 47, 1271–1277. doi: 10.1134/S1070428011090016
Moskalik M.Y., Garagan I.A., Astakhova V.V., Sterkhova I.V., Shainyan B.A., Tetrahedron. 2021, 88, 132145. doi: 10.1016/j.tet.2021.132145
Sokolova A.S., Putilova V.P., Yarovaya O.I., Zybkina A.V., Mordvinova E.D., Zaykovskaya A.V., Shcherbakov D.N., Orshanskaya I.R., Sinegubova E.O., Esaulkova I.L., Borisevich S.S., Bormotov N.I., Shishkina L.N., Zarubaev V.V., Pyankov O.V., Maksyutov R.A., Salakhutdinov N.F. Molecules. 2021, 26, 2235. doi: 10.3390/molecules26082235
Benelli G., Govindarajan M., Rajeswary M., Vaseeharan B., Alyahya S.A., Alharbi N.S., Kadaikunnan S., Khaled J.M., Maggi F. Ecotoxicol. Environ. Saf. 2018, 148, 781–786. doi: 10.1016/j.ecoenv.2017.11.044
Garagan I.A., Moskalik M.Yu., Sterkhova I.V., Ganin A.S. Molbank. 2023, 2, M1645. doi: 10.3390/M1645
Kiyokawa K., Kosaka T., Minakata S. Org. Lett. 2013, 15, 4858–4861. doi: 10.1021/ol402276f
Moskalik M.Y., Ganin A.S., Shainyan B.A. Int. J. Mol. Sci. 2023, 24, 15947. doi: 10.3390/ijms242115947
Filimonov D.A., Lagunin A.A., Gloriozova T.A., Rudik A.V., Druzhilovskii D.S., Pogodin P.V., Poroikov V.V. Chem. Heterocycl. Compd. 2014, 50, 444–457. doi: 10.1007/s10593-014-1496-1