AlMe3-Promoted Formation of Amides from Acids and Amines

In the presence of AlMe3, amines can be directly coupled with acids through dimethylaluminum amide intermediates to form the corresponding amides. A wide range of amines and acids including less nucleophilic amines, bulky amines, unprotected secondary amino acids, and acids with poor solubility were...

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Bibliographic Details
Published in:Organic letters 2012-01, Vol.14 (1), p.214-217
Main Authors: Li, Jianqing, Subramaniam, Krishnananthan, Smith, Daniel, Qiao, Jennifer X, Li, Jie Jack, Qian-Cutrone, Jingfang, Kadow, John F, Vite, Gregory D, Chen, Bang-Chi
Format: Article
Language:eng ; jpn
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Summary:In the presence of AlMe3, amines can be directly coupled with acids through dimethylaluminum amide intermediates to form the corresponding amides. A wide range of amines and acids including less nucleophilic amines, bulky amines, unprotected secondary amino acids, and acids with poor solubility were coupled smoothly to give the desired products in 55–98% yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol203007s