Cyanation ofN-Acylhydrazones with Trimethylsilyl Cyanide Promoted by a Brønsted Base and a Lewis Acid
作者:Hideyuki Konishi、Chikako Ogawa、Masaharu Sugiura、Shū Kobayashi
DOI:10.1002/adsc.200505272
日期:2005.12
Cyanation of N-acylhydrazones using trimethylsilyl cyanide (TMSCN) proceeded well in the presence of an amine to afford the corresponding α-hydrazinonitriles in high yields. For less reactive substrates, the combined use of an amine and a catalytic amount of scandium triflate [Sc(OTf)3] was effective to promote the reactions. The mechanistic study suggested that the amine worked as a Brønsted base
的氰化Ñ -acylhydrazones使用胺,得到相应的α-hydrazinonitriles高产率的存在下进行以及三甲基硅烷基氰化物(TMSCN)。对于反应性较低的底物,胺和催化量的三氟甲磺酸[[Sc(OTf)3 ]的组合使用可有效促进反应。机理研究表明,胺作为布朗斯台德碱起作用。