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Molecular Engineering of beta-Substituted Oxoporphyrinogens forHydrogen-Bond Donor Catalysis

Chahal, Mandeep Kaur, Payne, Daniel T., Matsushita, Yoshitaka, Labuta, Jan, Ariga, Katsuhiko, Hill, Jonathan P. (2020) Molecular Engineering of beta-Substituted Oxoporphyrinogens forHydrogen-Bond Donor Catalysis. European Journal of Organic Chemistry, 2020 (1). pp. 82-90. ISSN 1434-193X. E-ISSN 1099-0690. (doi:10.1002/ejoc.201901706) (Access to this publication is currently restricted. You may be able to access a copy if URLs are provided) (KAR id:103841)

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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.

Item Type: Article
DOI/Identification number: 10.1002/ejoc.201901706
Subjects: Q Science > QD Chemistry
Divisions: Divisions > Division of Natural Sciences > Chemistry and Forensics
Depositing User: Mandeep Kaur Chahal
Date Deposited: 09 Nov 2023 13:27 UTC
Last Modified: 10 Nov 2023 11:41 UTC
Resource URI: (The current URI for this page, for reference purposes)

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Chahal, Mandeep Kaur.

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