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Metal-free formal synthesis of phenoxazine
Kervefors, Gabriella, Becker, Antonia, Dey, Chandan, Olofsson, Berit
Beilstein Journal of Organic Chemistry. 14:1491-1497
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| Title | Metal-free formal synthesis of phenoxazine |
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| Authors | Kervefors, Gabriella, Becker, Antonia, Dey, Chandan, Olofsson, Berit |
| Source |
Beilstein Journal of Organic Chemistry. 14:1491-1497
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| 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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