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

Authors: Ganin A.S.¹, Garagan I.A.¹, Sobyanina M.M.¹, Moskalik M.Y.¹
Affiliations:
1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences
Issue: Vol 60, No 9 (2024)
Pages: 973-983
Section: Articles
URL: https://kld-journal.fedlab.ru/0514-7492/article/view/681712
DOI: https://doi.org/10.31857/S0514749224090048
EDN: https://elibrary.ru/QNWGCG
ID: 681712

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Abstract

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.

Keywords

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

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