Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland.
Nat Protoc. 2017 Feb;12(2):417-428. doi: 10.1038/nprot.2016.175. Epub 2017 Jan 26.
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 (CO) as the carbon source, hydrosilanes as reductants and N-heterocyclic carbenes (NHCs) as catalysts. Using CO 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.
胺的 N-甲酰化和 N-甲基化是重要的反应，可用于生产广泛的关键中间体和化合物。本协议描述了使用二氧化碳 (CO) 作为碳源、硅烷作为还原剂和 N-杂环卡宾 (NHC) 作为催化剂对伯胺和仲胺进行环境友好的 N-甲酰化和 N-甲基化。使用 CO 作为试剂具有成本低和毒性可忽略不计的优点。然而，催化剂对空气敏感，必须在使用前新鲜制备；因此，描述了制备和操作催化剂的技术。本协议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，具体取决于底物的性质。
