BJOC - Metal-free formal synthesis of phenoxazine

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Supporting Information File 1: Experimental details for the synthesis of starting materials and products, analytical data for products 2, 3, 5a, 7a, 9 and 11.
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Supporting Information File 2: NMR spectra for products 2, 3, 5a, 7a and 11.
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Metal-free formal synthesis of phenoxazine

Gabriella Kervefors, Antonia Becker, Chandan Dey and Berit Olofsson

Beilstein J. Org. Chem. 2018, 14, 1491–1497. https://doi.org/10.3762/bjoc.14.126

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Kervefors, G.; Becker, A.; Dey, C.; Olofsson, B. Beilstein J. Org. Chem. 2018, 14, 1491–1497. doi:10.3762/bjoc.14.126

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TY  - JOUR
A1  - Kervefors, Gabriella
A1  - Becker, Antonia
A1  - Dey, Chandan
A1  - Olofsson, Berit
T1  - Metal-free formal synthesis of phenoxazine
JF  - Beilstein Journal of Organic Chemistry
PY  - 2018///
VL  - 14
SP  - 1491
EP  - 1497
SN  - 1860-5397
DO  - 10.3762/bjoc.14.126
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.14.126
KW  - arylation
KW  - cyclization
KW  - diaryl ether
KW  - diaryliodonium salt
KW  - phenol
N2  - 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.
ER  -

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