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Synthesis of Triarylmethanes by Decarbonylation of 3,3-Diaryl Benzofuranones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-20 , DOI: 10.1021/acs.joc.9b03433
Zhi Tang 1 , Lingteng Peng 1 , Yu Yuan 1 , Tianjing Li 1 , Renhua Qiu 1 , Nobuaki Kambe 1, 2, 3
Affiliation  

A simple protocol for the synthesis of triarylmethane derivatives with three different (hetero)aryl groups by decarbonylation of 3,3-diaryl benzofuranones, which can easily be prepared via arylation of benzofuranones, was developed. The reaction proceeds on heating in dimethylformamide (DMF) in the presence of CH3ONa and water to generate the products in good to excellent yields. This reaction can be easily scaled up to give a triarylmethane in a gram scale. Further chemical manipulation of the products enabled useful transformations of the phenol ring, including reduction, arylation, cyclization, etc.

中文翻译:

3,3-二芳基苯并呋喃酮的脱羰合成三芳基甲烷

开发了一种简单的方案,用于通过3,3-二芳基苯并呋喃酮的脱羰反应合成具有三个不同(杂)芳基的三芳基甲烷衍生物,该方法很容易通过苯并呋喃酮的芳基化反应制备。在CH 3 ONa和水的存在下,在二甲基甲酰胺(DMF)中加热,使反应进行,从而以高至优异的产率生成产物。该反应可以容易地按比例放大以得到克级的三芳基甲烷。对产物进行进一步的化学处理可实现酚环的有用转化,包括还原,芳基化,环化等。
更新日期:2020-04-24
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