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Issue 1, 2018
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Conformational control of nonplanar free base porphyrins: towards bifunctional catalysts of tunable basicity

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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

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Publication details

The article was received on 19 Oct 2017, accepted on 14 Nov 2017 and first published on 11 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC08099A
Chem. Commun., 2018,54, 26-29
  • Open access: Creative Commons BY license
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    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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