Metal-free formal synthesis of phenoxazine

Autor: Gabriella Kervefors, Antonia Becker, Chandan Dey, Berit Olofsson
Jazyk: angličtina
Rok vydání: 2018
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 14, Iss 1, Pp 1491-1497 (2018)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.14.126
Popis: 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.
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