Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis.
Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis.
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DOI：
10.1002/anie.201708216
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发表时间：
2017-11
影响因子：
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通讯作者：
M. Pelckmans;Walter Vermandel;Frederik Van Waes;K. Moonen;B. Sels
中科院分区：
文献类型：
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作者：
M. Pelckmans;Walter Vermandel;Frederik Van Waes;K. Moonen;B. Sels
短胺，例如乙醇胺和乙二胺，是当今散装和精细化学品工业中的重要化合物。不幸的是，目前这些化学品的工业制造依赖于化石资源，并且在处理爆炸性或有毒中间体时需要严格的安全措施。受醛缩酶优雅工作机制的启发，开发了一种新颖的非均相催化过程——还原氨解，用于在低温下从碳水化合物高效生产短胺。在没有溶剂且温度低于 405 K 的情况下，一步合成了含有生物来源的 C2 碳主链的高价值生物基胺，收率高达 87 C%。多种可用的伯和仲烷基胺和链烷醇胺可以与碳水化合物反应形成相应的 C2-二胺。因此，所提出的还原氨解是可持续合成短链、无环生物胺的一种有前途的策略。
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.