Activation of Phenyl-N-(triflyl)imino-λ3-iodane by Metal Salts in Reactions with Alkenes
- 作者: Ganin A.S.1, Garagan I.A.1, Sobyanina M.M.1, Moskalik M.Y.1
- 
							隶属关系: 
							- A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
 
- 期: 卷 60, 编号 9 (2024)
- 页面: 973-983
- 栏目: Articles
- URL: https://rjeid.com/0514-7492/article/view/681712
- DOI: https://doi.org/10.31857/S0514749224090048
- EDN: https://elibrary.ru/QNWGCG
- ID: 681712
如何引用文章
详细
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.
全文:
 
												
	                        作者简介
A. Ganin
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
							编辑信件的主要联系方式.
							Email: ganin@irioch.irk.ru
				                	ORCID iD: 0000-0003-1626-795X
				                																			                												                	俄罗斯联邦, 							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
				                																			                												                	俄罗斯联邦, 							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
				                																			                												                	俄罗斯联邦, 							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
				                					                																			                												                	俄罗斯联邦, 							ul. Favorskogo, 1, Irkutsk, 664033						
参考
- 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
补充文件
 
				
			 
						 
						 
						 
						 
					

 
  
  
  电邮这篇文章
			电邮这篇文章 
 开放存取
		                                开放存取 ##reader.subscriptionAccessGranted##
						##reader.subscriptionAccessGranted##









