Abstract
AbstractHerein a practical and efficient potassium tert-butoxide (KO
t
Bu)-facilitated amination of carboxylic acids with N,N-dimethylamine is described. In the presence of catalytic amount of KO
t
Bu, a variety of aliphatic and aromatic carboxylic acids are transformed to N,N-dimethylamides using DMF as the dimethylamine reagent with the assistance of trimethylacetic anhydride. The applicability of this protocol is demonstrated by late-stage dimethylamidation of complex drug molecules. A plausible reaction mechanism involving KO
t
Bu-facilitated in situ amine generation from formamide decomposition and anhydride-mediated condensation is proposed on the basis of mechanistic investigations.
Funder
National Natural Science Foundation of China
Fundamental Research Funds for Central Universities of the Central South University
Wuhan University
Subject
Organic Chemistry,Catalysis
Cited by
2 articles.
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