Selective Synthesis of THF-Derived Amines from Biomass-Derived Carbonyl Compounds

Selective transformation of biomass or biomass-based feedstocks into value-added amines is highly desirable and constitutes one of the most important challenges in catalysis. As of today, only few amination studies have been reported on biobased substrates, targeting mainly the reductive amination o...

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Bibliographic Details
Published inACS catalysis Vol. 9; no. 10; pp. 8893 - 8902
Main Authors Jiang, Shi, Ma, Changru, Muller, Eric, Pera-Titus, Marc, Jérôme, François, De Oliveira Vigier, Karine
Format Journal Article
LanguageEnglish
Published American Chemical Society 04.10.2019
Subjects
Catalysis
Chemical Sciences
palladium
biomass
aldol condensation
amination
furfural
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Summary:Selective transformation of biomass or biomass-based feedstocks into value-added amines is highly desirable and constitutes one of the most important challenges in catalysis. As of today, only few amination studies have been reported on biobased substrates, targeting mainly the reductive amination of small platform molecules issued directly from biomass. Here we present a simple and highly efficient system using NH3 or amines as a nitrogen source and molecular hydrogen as reducing agent for the transformation of furan-derived ketones into tetrahydrofuran (THF)-derived amines over Pd/Al2O3 (up to 98% yield). Detailed analysis of the reaction system provided insight into the reaction mechanism. To further realize the production of THF-derived amines, a one-pot, two-step strategy combining C–C and C–N condensation reactions was attempted. A high yield (85%) toward 5-methyl-1-(tetrahydrofuran-2-yl)­hexan-3-amine could be successfully achieved starting directly from furfural.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b03413