Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis

Modular Counter-Fischer–Indole Synthesis through Radical-Enolate Coupling

Organic Letters ◽

10.1021/acs.orglett.1c00003 ◽

2021 ◽

Vol 23 (3) ◽

pp. 1096-1102

Author(s):

Hyunho Chung ◽

Jeongyun Kim ◽

Gisela A. González-Montiel ◽

Paul Ha-Yeon Cheong ◽

Hong Geun Lee

Keyword(s):

Fischer Indole Synthesis ◽

Indole Synthesis

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Ultrathin Amorphous/Crystalline Heterophase Rh and Rh Alloy Nanosheets as Tandem Catalysts for Direct Indole Synthesis

Advanced Materials ◽

10.1002/adma.202006711 ◽

2021 ◽

pp. 2006711

Author(s):

Jingjie Ge ◽

Peiqun Yin ◽

Ye Chen ◽

Hongfei Cheng ◽

Jiawei Liu ◽

...

Keyword(s):

Indole Synthesis

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Fischer Indole Synthesis in the Gas Phase, the Solution Phase, and at the Electrospray Droplet Interface

Journal of the American Society for Mass Spectrometry ◽

10.1007/s13361-017-1597-z ◽

2017 ◽

Vol 28 (7) ◽

pp. 1359-1364 ◽

Cited By ~ 14

Author(s):

Ryan M. Bain ◽

Stephen T. Ayrton ◽

R. Graham Cooks

Keyword(s):

Gas Phase ◽

Solution Phase ◽

Fischer Indole Synthesis ◽

Indole Synthesis

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Metal-free formal synthesis of phenoxazine

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.14.126 ◽

2018 ◽

Vol 14 ◽

pp. 1491-1497 ◽

Cited By ~ 4

Author(s):

Gabriella Kervefors ◽

Antonia Becker ◽

Chandan Dey ◽

Berit Olofsson

Keyword(s):

Reaction Time ◽

Transition Metal ◽

Formal Synthesis ◽

Metal Free ◽

Diaryl Ether ◽

Diaryliodonium Salt ◽

Moderate Yield ◽

Stable Iodine

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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