Issue 68, 2023

Divergent synthesis of pyrrole carboxamides from pyrrole carboxaldehyde and formamides/amines via oxidative amidation involving pyrrole acyl radicals

Abstract

A non-traditional approach for the synthesis of pyrrole carboxamides from pyrrole carboxaldehyde and formamides or amines with catalytic amounts of nBu4NI and TBHP as oxidants is reported herein. The method is operationally simple providing straightforward access to primary, secondary, and tertiary pyrrole carboxamides in good to excellent yields utilizing inexpensive reagents under mild conditions. Unlike traditional amidations that involve ionic reactions, a mechanistic study of our current method unveils the involvement of 2- or 3-pyrrole acyl radicals that are otherwise rarely postulated. The applicability of the current method is further demonstrated in the synthesis of a drug-like compound, i.e., an optically pure carboetomidate amide.

Graphical abstract: Divergent synthesis of pyrrole carboxamides from pyrrole carboxaldehyde and formamides/amines via oxidative amidation involving pyrrole acyl radicals

Supplementary files

Article information

Article type
Communication
Submitted
08 Jūn. 2023
Accepted
26 Jūl. 2023
First published
26 Jūl. 2023

Chem. Commun., 2023,59, 10259-10262

Divergent synthesis of pyrrole carboxamides from pyrrole carboxaldehyde and formamides/amines via oxidative amidation involving pyrrole acyl radicals

J. K. Laha, S. Panday, J. P. Weber and M. Breugst, Chem. Commun., 2023, 59, 10259 DOI: 10.1039/D3CC02766J

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