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

submitted on 20.08.2019, 02:12 and posted on 20.08.2019, 18:16 by Mandeep K. Chahal, Daniel Payne, Yoshitaka Matsushita, Jan Labuta, Katsuhiko Ariga, Jonathan P. Hill

A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens with 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 report the first example of non-planar OxPs as hydrogen-bond donor catalysts. 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.


This work was partly supported by World Premier International Research Center Initiative (WPI Initiative), MEXT, Japan. The authors are grateful to Japan Society for the Promotion of Science (JSPS) for a JSPS Fellowship (to D.T.P.). This work was also partially supported by JSPS KAKENHI Grant No. JP16H06518 (Coordination Asymmetry), Grant No. 19K05229, and CREST, JST Grant No. JPMJCR1665.


Email Address of Submitting Author


National Institute for Materials Science



ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no competing financial interest.


Read the published paper

in European Journal of Organic Chemistry