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Mild Esterification of Carboxylic Acids via Continuous Flow Diazotization of Amines

Clément Audubert and Hélène Lebel*

*Département de Chimie, Center for Green Chemistry and Catalysis, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montréal, Québec, Canada H3C 3J7, Email: helene.lebelumontreal.ca

C. Audubert, H. Lebel, Org. Lett., 2017, 19, 4407-4410.

DOI: 10.1021/acs.orglett.7b02231 (free Supporting Information)


Abstract

A continuous flow protocol for the diazotization of amines with 1,3-propanedinitrite in THF enables the synthesis of esters in high yields from various carboxylic acids in 20 min at 90°C. The reaction conditions were compatible with many functional groups, such as nitrogen-containing heterocycles, alkynes, alkenes, alcohols, and phenols.

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proposed mechanism



Key Words

flow chemistry, esters


ID: J54-Y2017