Issue 1, 2017

Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles

Abstract

α-Difluoromethyl pyrroles were found to be stable while N-protected with an electron-withdrawing group. Due to the propensity of pyrroles to access azafulvenium-like intermediates, the C–F bonds of an α-difluoromethyl substituent are labile under hydrolytic conditions. The presence of certain electron-withdrawing substituents about the pyrrolic ring can accelerate this process, as determined through a kinetic comparison of the deprotection and subsequent hydrolysis reactions of N-protected β-aryl α-difluoromethyl pyrroles.

Graphical abstract: Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles

Supplementary files

Article information

Article type
Paper
Submitted
05 Jul 2016
Accepted
04 Nov 2016
First published
14 Nov 2016

Org. Biomol. Chem., 2017,15, 144-152

Author version available

Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles

J. A. Melanson, C. Figliola, D. A. Smithen, A. K. Kajetanowicz and A. Thompson, Org. Biomol. Chem., 2017, 15, 144 DOI: 10.1039/C6OB01441K

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