Selective N-Arylation of Aminobenzanilides under Mild Conditions Using Triarylbismuthanes

Diarylamines are prepared selectively in good yields under mild conditions by treatment of aminobenzanilides with triarylbismuthanes in the presence of copper(II) acetate and triethylamine. Arylation under these conditions occurs preferentially at the amino- rather than the amide-nitrogen of the ben...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-11, Vol.65 (23), p.7747-7749
Main Author: Sorenson, Roderick J
Format: Article
Language:English
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Summary:Diarylamines are prepared selectively in good yields under mild conditions by treatment of aminobenzanilides with triarylbismuthanes in the presence of copper(II) acetate and triethylamine. Arylation under these conditions occurs preferentially at the amino- rather than the amide-nitrogen of the benzanilide. Thus, heating an aminobenzanilide in dichloromethane under reflux in the presence of 1 equiv each of a triarylbismuthane, triethylamine, and copper(II) acetate affords the diarylamine in good yields. This method thereby provides a mild and expeditious route to functionalized diarylamines.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000614m