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Metal-Free Oxyacetoxylation of Arylynamines and Ynamides to Construct α-Acetoxyl Amides
Long, R. ; Huang, S. ; Wu, Han-Kui ; Iqbal, Naila ; Wu, Na
Long, R.
Huang, S.
Wu, Han-Kui
Iqbal, Naila
Wu, Na
Publication Date
2023
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© 2023 Wiley. This is the peer-reviewed version of the following article: Long R, Huang S, Wu H-K et al (2023) Metal-Free Oxyacetoxylation of Arylynamines and Ynamides to Construct α-Acetoxyl Amides. European Journal of Organic Chemistry. vol 26(32): e202300393 which has been published in final form at https://doi.org/10.1002/ejoc.202300393. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
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2023-06-27
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Abstract
Ynamides/arylynamines are challenging substrates for oxyacetoxylation, especially due to various reactive sites of N-heteroaryl ring. Herein we report a metal-free PhI(OAc)2-mediated oxyacetoxylation of arylynamines / ynamides to provide α-acetoxyl amides in good to excellent yields. The transformation completes in a short time to afford solely the product without functionalising N-heteroaryl moiety, in a highly regio- and chemo-selective manner through β-iodo keteneiminium intermediate.
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Long R, Huang S, Wu H-K et al (2023) Metal-Free Oxyacetoxylation of Arylynamines and Ynamides to Construct α-Acetoxyl Amides. European Journal of Organic Chemistry. 26(32): e202300393.
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