Molecular Engineering of β‐Substituted Oxoporphyrinogens for Hydrogen‐Bond Donor Catalysis

Chahal, Mandeep K.; Payne, Daniel T.; Matsushita, Yoshitaka; Labuta, Jan; Ariga, Katsuhiko and Hill, Jonathan P. (2020). Molecular Engineering of β‐Substituted Oxoporphyrinogens for Hydrogen‐Bond Donor Catalysis. European Journal of Organic Chemistry, 2020(1) pp. 82–90.

DOI: https://doi.org/10.1002/ejoc.201901706

Abstract

A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.

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