cs9b03413_si_001.pdf (3.5 MB)
Selective Synthesis of THF-Derived Amines from Biomass-Derived Carbonyl Compounds
journal contribution
posted on 2019-08-30, 19:44 authored by Shi Jiang, Changru Ma, Eric Muller, Marc Pera-Titus, François Jérôme, Karine De Oliveira VigierSelective
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.