Construction of Highly Functionalized 2-Styrylfurans by N-Heterocyclic Carbene/Brønsted Acid Catalysis
Izabela Barańska, Borys Ośmiałowski, Katarzyna Rafińska, Zbigniew Rafiński
Abstract
This research presents an original method for synthesizing styrylfurans using N-heterocyclic carbenes (NHCs) and Brønsted acid catalysis. By exploiting 2,4-dioxoesters as conjugated 1,3-dicarbonyls, we have developed a technique allowing the efficient formation of highly functionalized styrylfurans with interesting photochemical properties, through a NHC-catalyzed cross-benzoin reaction followed by a Brønsted acid-driven Paal-Knorr-like condensation. This approach permits the integration of various substituents on the furan ring, with preliminary biological studies indicating potential as fluorescent dyes.
Topics & Concepts
ChemistryCarbeneCatalysisBrønsted–Lowry acid–base theoryFuranConjugated systemRing (chemistry)Combinatorial chemistryBenzoinOrganic chemistryUmpolungFluorescencePolymerQuantum mechanicsNucleophilePhysicsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms