N-formylation and N-methylation of amines using metal-free N-heterocyclic carbene catalysts and CO2 as carbon source
N-formylation and N-methylation of amines using metal-free N-heterocyclic carbene catalysts and CO2 as carbon source
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DOI：
10.1038/nprot.2016.175
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发表时间：
2017-02-01
期刊：
影响因子：
14.8
通讯作者：
Dyson, Paul J.
中科院分区：
文献类型：
--
作者：
Bobbink, Felix D.;Das, Shoubhik;Dyson, Paul J.
胺的N-甲基化和N-甲基化是重要的反应，用于生产广泛的关键中间体和化合物。该方案描述了使用二氧化碳（CO2）作为碳源、氢硅烷作为还原剂和N-杂环卡宾（NHC）作为催化剂的伯胺和仲胺的环境友好的N-取代和N-甲基化。使用CO2作为试剂具有成本低和毒性小的优点。然而，催化剂是空气敏感的，必须在使用前新鲜产生;因此，用于制备和操作催化剂的技术进行了描述。本方案中描述的合成方法不使用任何有毒试剂;使用适当的催化剂，可以高选择性地获得N-甲酰化或N-甲基化产物。催化剂制备和并行进行几个催化反应的总时间为15-48小时，这取决于底物的性质。
N-formylation and N-methylation of amines are important reactions that are used to produce a wide range of key intermediates and compounds. This protocol describes the environmentally benign N-formylation and N-methylation of primary and secondary amines using carbon dioxide (CO2) as the carbon source, hydrosilanes as reductants and N-heterocyclic carbenes (NHCs) as catalysts. Using CO2 as a reagent has the advantage of low cost and negligible toxicity. However, the catalyst is air-sensitive and must be generated fresh before use; consequently, the techniques used to prepare and manipulate the catalyst are described. The synthetic approach described in this protocol does not use any toxic reagents; using the appropriate catalyst, N-formylated or N-methylated products can be obtained with high selectivity. The overall time for catalyst preparation and for conducting several catalytic reactions in parallel is 15-48 h, depending on the nature of the substrates.