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: 
							
- 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://transsyst.ru/0514-7492/article/view/681712
 - DOI: https://doi.org/10.31857/S0514749224090048
 - EDN: https://elibrary.ru/QNWGCG
 - ID: 681712
 
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Resumo
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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Sobre autores
A. Ganin
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
							Autor responsável pela correspondência
							Email: ganin@irioch.irk.ru
				                	ORCID ID: 0000-0003-1626-795X
				                																			                												                	Rússia, 							ul. Favorskogo, 1, Irkutsk, 664033						
I. Garagan
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
														Email: ganin@irioch.irk.ru
				                	ORCID ID: 0000-0003-3024-798X
				                																			                												                	Rússia, 							ul. Favorskogo, 1, Irkutsk, 664033						
M. Sobyanina
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
														Email: ganin@irioch.irk.ru
				                	ORCID ID: 0000-0002-0361-0897
				                																			                												                	Rússia, 							ul. Favorskogo, 1, Irkutsk, 664033						
M. Moskalik
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
														Email: ganin@irioch.irk.ru
				                					                																			                												                	Rússia, 							ul. Favorskogo, 1, Irkutsk, 664033						
Bibliografia
- 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
 
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