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Low‐Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis
Author(s) -
Pelckmans Michiel,
Vermandel Walter,
Van Waes Frederik,
Moonen Kristof,
Sels Bert F.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201708216
Subject(s) - aminolysis , chemistry , organic chemistry , catalysis , primary (astronomy) , diamine , reductive amination , combinatorial chemistry , physics , astronomy
Short amines, such as ethanolamines and ethylenediamines, are important compounds in today's bulk and fine chemicals industry. Unfortunately, current industrial manufacture of these chemicals relies on fossil resources and requires rigorous safety measures when handling explosive or toxic intermediates. Inspired by the elegant working mechanism of aldolase enzymes, a novel heterogeneously catalyzed process—reductive aminolysis—was developed for the efficient production of short amines from carbohydrates at low temperature. High‐value bio‐based amines containing a bio‐derived C2 carbon backbone were synthesized in one step with yields up to 87 C%, in the absence of a solvent and at a temperature below 405 K. A wide variety of available primary and secondary alkyl‐ and alkanolamines can be reacted with the carbohydrate to form the corresponding C2‐diamine. The presented reductive aminolysis is therefore a promising strategy for sustainable synthesis of short, acyclic, bio‐based amines.