Metal-free formal synthesis of phenoxazine

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. Th...

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Autores principales: Kervefors, Gabriella, Becker, Antonia, Dey, Chandan, Olofsson, Berit
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6036965/
https://www.ncbi.nlm.nih.gov/pubmed/30013676
http://dx.doi.org/10.3762/bjoc.14.126
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author Kervefors, Gabriella
Becker, Antonia
Dey, Chandan
Olofsson, Berit
author_facet Kervefors, Gabriella
Becker, Antonia
Dey, Chandan
Olofsson, Berit
author_sort Kervefors, Gabriella
collection PubMed
description 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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spelling pubmed-60369652018-07-16 Metal-free formal synthesis of phenoxazine Kervefors, Gabriella Becker, Antonia Dey, Chandan Olofsson, Berit Beilstein J Org Chem Letter 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. Beilstein-Institut 2018-06-20 /pmc/articles/PMC6036965/ /pubmed/30013676 http://dx.doi.org/10.3762/bjoc.14.126 Text en Copyright © 2018, Kervefors et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Kervefors, Gabriella
Becker, Antonia
Dey, Chandan
Olofsson, Berit
Metal-free formal synthesis of phenoxazine
title Metal-free formal synthesis of phenoxazine
title_full Metal-free formal synthesis of phenoxazine
title_fullStr Metal-free formal synthesis of phenoxazine
title_full_unstemmed Metal-free formal synthesis of phenoxazine
title_short Metal-free formal synthesis of phenoxazine
title_sort metal-free formal synthesis of phenoxazine
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6036965/
https://www.ncbi.nlm.nih.gov/pubmed/30013676
http://dx.doi.org/10.3762/bjoc.14.126
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