Synthesis of picolinates via a cooperative vinylogous anomeric-based oxidation using UiO-66(Zr)-N(CH2PO3H2)2 as a catalyst

Saeed Babaee; Hassan Sepehrmansourie; Mahmoud Zarei; Mohammad Ali Zolfigol; Mojtaba Hosseinifard

doi:10.1039/d3ra03438k

Synthesis of picolinates via a cooperative vinylogous anomeric-based oxidation using UiO-66(Zr)-N(CH₂PO₃H₂)₂ as a catalyst

RSC Adv. 2023 Jul 25;13(32):22503-22511. doi: 10.1039/d3ra03438k. eCollection 2023 Jul 19.

Authors

Saeed Babaee¹, Hassan Sepehrmansourie¹, Mahmoud Zarei², Mohammad Ali Zolfigol¹, Mojtaba Hosseinifard³

Affiliations

¹ Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University Hamedan 6517838683 Iran +988138380709 +988138282807 zolfi@basu.ac.ir mzolfigol@yahoo.com.
² Department of Chemistry, Faculty of Science, University of Qom Qom 37185-359 Iran mahmoud8103@yahoo.com.
³ Department of Energy, Materials and Energy Research Center P.O. Box 31787-316 Karaj Iran.

Abstract

The anomeric effect highlights the significant influence of the functional group and reaction conditions on oxidation-reduction. This article successfully investigates the anomeric effect in the synthesis of picolinate and picolinic acid derivatives through a multi-component reaction involving 2-oxopropanoic acid or ethyl 2-oxopropanoate, ammonium acetate, malononitrile, and various aldehydes. To facilitate this process, we employed UiO-66(Zr)-N(CH₂PO₃H₂)₂ as a novel nanoporous heterogeneous catalyst. The inclusion of phosphorous acid tags on the UiO-66(Zr)-N(CH₂PO₃H₂)₂ offers the potential for synthesizing picolinates at ambient temperature.