5 years ago

Mild Esterification of Carboxylic Acids via Continuous Flow Diazotization of Amines

Mild Esterification of Carboxylic Acids via Continuous Flow Diazotization of Amines
Hélène Lebel, Clément Audubert
A new continuous flow protocol for the diazotization of methylamine with 1,3-propanedinitrite in THF is reported. The synthesis of methyl esters was achieved in high yields from a variety of carboxylic acids in 20 min at 90 °C. Additionally, this protocol was extended to other aryl and alkyl amines, namely secondary amines, to produce various substituted esters in high yield using 2-MeTHF as a solvent. The reaction conditions were compatible with many functional groups, namely nitrogen-containing heterocycles, alkynes, alkenes, alcohols, and phenols. Mechanistic investigations reveal that the reaction appears to proceed through a transient diazonium species rather than a diazo intermediate.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02231

DOI: 10.1021/acs.orglett.7b02231

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