Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction

Marek Moczulski; Ewelina Kowalska; Elżbieta Kuśmierek; Łukasz Albrecht; Anna Albrecht

doi:10.1039/d1ra05914a

Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction

RSC Adv. 2021 Aug 16;11(45):27782-27786. doi: 10.1039/d1ra05914a.

Authors

Marek Moczulski¹, Ewelina Kowalska¹, Elżbieta Kuśmierek², Łukasz Albrecht¹, Anna Albrecht²

Affiliations

¹ Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology Żeromskiego 116 90-924 Łódź Poland.
² Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology Żeromskiego 116 90-924 Łódź Poland anna.albrecht@p.lodz.pl.

Abstract

Doubly decarboxylative, photoredox synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones is described. The reaction involves two independent decarboxylation processes: the first one initiating the cycle and the second completing the process. Visible light, photoredox catalyst, base, anhydrous solvent and inert atmosphere constitute the key parameters for the success of the developed transformation. The protocol proved applicable for coumarin-3-carboxylic acids and chromone-3-carboxylic acids as well as N-(acyloxy)phthalimide which served as precursors of the corresponding alkyl radicals.