Angewandte Chemie International Edition · 2020 · 124 citations · 36 references
Natural SciencesChemical EngineeringChemistryCatalysisGreen ChemistryReaction EngineeringBiomass ConversionCatalytic MechanismsGreen CatalysisIndustrial CatalysisIndustrial Catalytic ProcessesZeolite CatalysisAmination ReactionsBiorefinery FeedstocksCatalytic Biomass ConversionEscherichia ColiLignocellulosic Biomass ConversionRenewable Feedstock ConversionTandem ReactionsZeolite Catalysts
Abstract Production of renewable, high‐value N‐containing chemicals from lignocellulose will expand product diversity and increase the economic competitiveness of the biorefinery. Herein, we report a single‐step conversion of furfural to pyrrole in 75 % yield as a key N‐containing building block, achieved via tandem decarbonylation–amination reactions over tailor‐designed Pd@S‐1 and H‐beta zeolite catalytic system. Pyrrole was further transformed into dl ‐proline in two steps following carboxylation with CO 2 and hydrogenation over Rh/C catalyst. After treating with Escherichia coli, valuable d ‐proline was obtained in theoretically maximum yield (50 %) bearing 99 % ee. The report here establishes a route bridging commercial commodity feedstock from biomass with high‐value organonitrogen chemicals through pyrrole as a hub molecule.
36
A sustainable catalytic pyrrole synthesis
Stefan Michlik, Rhett Kempe · Nature Chemistry · 2013 · 486 citations