Issue 1, 2018

Conformational control of nonplanar free base porphyrins: towards bifunctional catalysts of tunable basicity

Abstract

For the first time, free base and N-methylated porphyrins have been utilized as bifunctional organocatalysts in Michael additions and it was found that distortion of the macrocycle is a vital prerequisite for their catalytic activity. Conformational design has been used to tailor the properties of nonplanar porphyrins with regards to availability of the N–H units for hydrogen bonding (distortion-dependent hydrogen bonding) and the basicity of the heterocyclic groups. NMR spectroscopic- and catalyst screening studies provided insight into the likely mode of catalyst action. This unprecedented use of free base and N-substituted porphyrins as organocatalysts opens a new functional role for porphyrins.

Graphical abstract: Conformational control of nonplanar free base porphyrins: towards bifunctional catalysts of tunable basicity

Supplementary files

Article information

Article type
Communication
Submitted
19 Oct 2017
Accepted
14 Nov 2017
First published
11 Dec 2017
This article is Open Access
Creative Commons BY license

Chem. Commun., 2018,54, 26-29

Conformational control of nonplanar free base porphyrins: towards bifunctional catalysts of tunable basicity

M. Roucan, M. Kielmann, S. J. Connon, S. S. R. Bernhard and M. O. Senge, Chem. Commun., 2018, 54, 26 DOI: 10.1039/C7CC08099A

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