Issue 4, 2020

A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2H-azirines

Abstract

The reaction of o-nitroiodobenzene and mCPBA in acetic acid was found to afford a novel hypervalent iodine compound, in the structure of which both iodine(III) and iodine(V) moieties coexist. The nitro groups at the ortho phenyl positions were found to be crucial in stabilizing this uncommon structure. This novel hypervalent iodine(III/V) oxidant is proved to be effective in realizing the synthesis of 2-unsubstitued 2H-azirines via intramolecular oxidative azirination, which could not be efficiently achieved by the existing known hypervalent iodine reagents.

Graphical abstract: A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2H-azirines

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Nov 2019
Accepted
05 Dec 2019
First published
06 Dec 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 947-953

A new hypervalent iodine(III/V) oxidant and its application to the synthesis of 2H-azirines

G. Zhang, Y. Wang, J. Xu, J. Sun, F. Sun, Y. Zhang, C. Zhang and Y. Du, Chem. Sci., 2020, 11, 947 DOI: 10.1039/C9SC05536C

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