Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 14, Pages 3444-3447Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800336
Keywords
aliphatic amides; esterification; fluoride catalysis; generic catalyst system; metal-free
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Funding
- Science and Technology Planning Project of Guangdong Province [2017A010103017]
- National Natural Science Foundation of China [21272080]
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In recent years, it has been demonstrated that amide carbon-nitrogen bonds can be activated and selectively cleaved using transition metal catalysts. However, these methodologies have been restricted to specific amides; a one-to-one relationship exists between the catalytic system and the amides and also uses large amounts of transition-metal catalysts and ligands. Hence, we now report a general strategy for esterification of common amides using fluoride as a catalyst. This method shows high functional group tolerance, and notably it requires only a slight excess of the alcohol nucleophile, which is a rare case in transition-metal-free amide transformations. Moreover, this approach may provide a new understanding for further studies on esterification of amides and is expected to stimulate the development of alternative methods for direct functionalization of amides.
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