Influence of Pore Size in Benzoin Condensation of Furfural Using Heterogenized Benzimidazole Organocatalysts

Abstract

A designed N-heterocyclic carbene (NHC) catalyst was covalently anchored on a range of mesoporous and hierarchical supports, to study the influence of pore size in the benzoin condensation of furfural. The structural and spectroscopic characteristics of the anchored catalysts were investigated, also with the help of molecular dynamics simulations, in order to rationalize the degree of stability and recyclability of the heterogenized organocatalysts. Quantitative yields (99 %) and complete recyclability were maintained after several cycles, vindicating the design rationale.

Advancements in N-heterocyclic carbenes (NHCs) catalysis for benzoin reactions: A comprehensive review from past to present

“…In the benzoin condensation of furfural, hybrid catalysts exhibited varying degrees of stability, as reported by Miletto and colleagues in 2022 [59]. The NHC catalyst was composed of a benzimidazole covalently affixed to a variety of mesoporous and hierarchical supports.…”

Synthesis of amine derivatives from furoin and furil over a Ru/Al2O3 catalyst

“…10 Bim catalysts have been supported over silica and polymers with controlled mesoporosity, affording recyclable heterogeneous catalysts. 11 In the presence of a base ( e.g. , 1,8-diazabicylo-[5.4.0]undec-7-ene, DBU), supported bim catalysts can catalyze the self-condensation of FF into furoin with 96–99% yield over three consecutive runs.…”

Highly Efficient N‐Heterocyclic Carbene Precursor from Sterically Hindered Benzimidazolium Salt for Benzoin Condensation

“…In 2022, Robert et al . to understand how pore size affects furfural‘s benzoin condensation, they attached a custom NHC catalyst to different porous materials and studied the reaction [16] . In 2021 A. Washio et al .…”

“…[15b] In 2022, Robert et al to understand how pore size affects furfural's benzoin condensation, they attached a custom NHC catalyst to different porous materials and studied the reaction. [16] In 2021 A. Washio et al works on the p-anisaldehyde by using N-heterocyclic carbene catalysts such as Vitamin B1, and deracemization via dynamic crystallization. [17] In Figure 1 mentioned about previously reported NHC catalyzed benzoin condensation reactions.…”