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Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles

Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles A convenient procedure for oxidative cycloaddition of aldoximes with nitriles using stoichiometric or catalytic amounts of hypervalent iodine(III) reagent IBA‐OTf (2‐iodosylbenzoic acid triflate) has been developed. This efficient procedure works well for the preparation of various 1,2,4‐oxadiazoles in generally high yields under mild reaction conditions. The actual oxidant in this reaction, IBA‐OTf, is prepared from 2‐iodosylbenzoic acid (IBA) and trifluoromethanesulfonic acid (TfOH) or it can be generated in situ from 2‐iodobenzoic acid and m‐chloroperoxybenzoic acid (m‐CPBA) in the presence of TfOH. The nature of hydroxy(aryl)iodonium species, generated in situ from 2‐iodobenzoic acid, m‐CPBA, and TfOH under catalytic reaction conditions, has been confirmed by 1H NMR spectroscopy, ESI‐mass spectrometry, and by X‐ray diffraction. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

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References (45)

Publisher
Wiley
Copyright
© 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201600247
Publisher site
See Article on Publisher Site

Abstract

A convenient procedure for oxidative cycloaddition of aldoximes with nitriles using stoichiometric or catalytic amounts of hypervalent iodine(III) reagent IBA‐OTf (2‐iodosylbenzoic acid triflate) has been developed. This efficient procedure works well for the preparation of various 1,2,4‐oxadiazoles in generally high yields under mild reaction conditions. The actual oxidant in this reaction, IBA‐OTf, is prepared from 2‐iodosylbenzoic acid (IBA) and trifluoromethanesulfonic acid (TfOH) or it can be generated in situ from 2‐iodobenzoic acid and m‐chloroperoxybenzoic acid (m‐CPBA) in the presence of TfOH. The nature of hydroxy(aryl)iodonium species, generated in situ from 2‐iodobenzoic acid, m‐CPBA, and TfOH under catalytic reaction conditions, has been confirmed by 1H NMR spectroscopy, ESI‐mass spectrometry, and by X‐ray diffraction.

Journal

Asian Journal of Organic ChemistryWiley

Published: Sep 1, 2016

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