A catalytic approach via retro-aldol condensation of glucose to furanic compounds

Abstract

The synthesis of new type furan-based compounds other than 5-hydroxymethylfurfural from glucose is a very attractive yet underexploited strategy. We report here a catalytic conversion of glucose with acetylacetone (acac)...

Biomass to Aromatic Amine Module: Alkali Catalytic Conversion of N‐Acetylglucosamine into Unsubstituted 3‐Acetamidofuran by Retro‐Aldol Condensation

“…Due to the instability of glycolaldehyde under reaction conditions and the rapid dehydration properties of NAE (NAG conversion into 3AF is complete within 20 min), it is difficult to directly detect these intermediates. Inspired by a recent study conducted by Repo, [38] we sought to trap the intermediate glycolaldehyde in situ with acetylacetone to obtain the corresponding furan 2‐methyl‐3‐acetylfuran (MAF). Satisfyingly, MAF was detected under the Ba(OH) 2 reaction conditions (Figure 6).…”

“…To mechanistically study the NAG transformation into 3AF, acetylacetone was used as a trapping agent in situ to gain the corresponding products based on the method reported by Repo and co‐workers [38] . The NAG catalyzed by Ba(OH) 2 −H 3 BO 3 −NaCl or H 2 MoO 4 were conducted at 180 °C for 20 min in DMF/acetylacetone or H 2 O/acetylacetone.…”

Conversion of biomass-derived sugars to 1,1,2-trialkoxyethane via a [2 + 4] retro-aldol reaction over alkaline and alkaline earth metal salts of phosphotungstic acid

“…It has been known that converting glucose to TriEE takes a few steps as shown in Scheme 2. 12,29 First, glucose undergoes a [2 + 4] retro-aldol condensation reaction to form GA and erythrose, and the latter could further go through a [2 + 2] retroaldol condensation reaction to generate two molecules of GA. 30 GA takes part in the acetalization reaction with ethanol and forms hemiacetal (1-ethoxyethane-1,2-diol) and GDEA. Brønsted acids are acknowledged as effective catalysts for the hemiacetalization and acetalization reactions.…”

Near quantitative conversion of xylose into bisfuran

“…Recently, we reported the synthesis of substituted furanic compounds with good yields from glucose and acetylacetone (acac) via a cascade type retro-aldol condensation and GG reaction. 45 Acac is seen as a sustainable component in the reaction as it is available from glucose via chemical transformation or biosynthetic routes. 46,47 During the continuing research course, we observed a new type of bisfuranic compound obtained from xylose.…”