Direct Thioamination of Cyclohexanones via Difunctionalization with Thiophenol and Aniline

A synthetic method of o‐sulfanylanilines from cyclohexanones, amines, and thiophenols under transition‐metal‐free conditions is disclosed. This is the first report on the direct thioamination of cyclohexanones via N‐iodosuccinimide (NIS) promoted oxidative dehydroaromatization. Non‐aromatic cyclohex...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-07, Vol.364 (13), p.2205-2210
Main Authors: Tang, Minli, Zhang, Li, Mao, Guojiang, Xiao, Fuhong, Shao, Wen, Deng, Guo‐Jun
Format: Article
Language:English
Subjects:
Amines
Aniline
Aromatization
Cyclohexanone
Dehydrogenation
Metal-free
Multicomponent reactions
Oxidizing agents
Oxygenation
Thiophenol
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Summary:A synthetic method of o‐sulfanylanilines from cyclohexanones, amines, and thiophenols under transition‐metal‐free conditions is disclosed. This is the first report on the direct thioamination of cyclohexanones via N‐iodosuccinimide (NIS) promoted oxidative dehydroaromatization. Non‐aromatic cyclohexanones were smoothly dehydrogenated, and acted as an aryl source using oxygen as a green oxidant. The capacity of the resultant o‐sulfanylanilines for synthesis of N‐arylphenothiazines has been further demonstrated.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200365