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Metal-free formal synthesis of phenoxazine
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-7975-4582
2018 (English)In: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 14, p. 1491-1497Article in journal (Refereed) Published
Abstract [en]

A transition metal-free formal synthesis of phenoxazine is presented. The key step of the sequence is a high-yielding O-arylation of a phenol with an unsymmetrical diaryliodonium salt to provide an ortho-disubstituted diaryl ether. This species was cyclized to acetylphenoxazine in moderate yield. The overall yield in the three-step sequence is 72% based on recovered diaryl ether. An interesting, unusually stable iodine(III) intermediate in the O-arylation was observed by NMR and could be converted to the product upon longer reaction time.

Place, publisher, year, edition, pages
2018. Vol. 14, p. 1491-1497
Keywords [en]
arylation, cyclization, diaryl ether, diaryliodonium salt, phenol
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-158249DOI: 10.3762/bjoc.14.126ISI: 000435917200001PubMedID: 30013676OAI: oai:DiVA.org:su-158249DiVA, id: diva2:1238246
Funder
Swedish Research CouncilCarl Tryggers foundation Available from: 2018-08-13 Created: 2018-08-13 Last updated: 2018-09-07Bibliographically approved

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Kervefors, GabriellaBecker, AntoniaDey, ChandanOlofsson, Berit
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