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

Bibliografiske detaljer
Parent link:Asian Journal of Organic Chemistry
Vol. 5, iss. 9.— 2016.— [P. 1128–1133]
Institution som forfatter: Национальный исследовательский Томский политехнический университет Физико-технический институт Кафедра общей физики
Andre forfattere: Yoshimura A. Akira, Nguyen Khiem, Klasen S. C. Scott, Postnikov P. S. Pavel Sergeevich, Yusubov M. S. Mekhman Suleiman-Ogly (Suleimanovich), Saito A. Akio, Nemykin V. N. Viktor Nikolaevich, Zhdankin V. V. Viktor
Summary:Title screen
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.
Режим доступа: по договору с организацией-держателем ресурса
Sprog:engelsk
Udgivet: 2016
Fag:
электронный ресурс
труды учёных ТПУ
Online adgang:http://dx.doi.org/10.1002/ajoc.201600247
Format: Electronisk Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=651213
Beskrivelse
Summary:Title screen
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.
Режим доступа: по договору с организацией-держателем ресурса
DOI:10.1002/ajoc.201600247

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