Zhang Zhenming, Fu Bei, Wang Hui, Chen Han, Tu Yongliang, Zhao Junfeng
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, Jiangxi, P. R. China.
J Org Chem. 2020 Apr 17;85(8):5245-5254. doi: 10.1021/acs.joc.9b03305. Epub 2020 Apr 2.
An efficient base-promoted tandem reaction between vinyl 1,1-dichlorides and secondary sulfonamides with ynamide as the key intermediate is described. This method provides a facile approach to ()-1,2-endiamide and aryl 1,1-endiamide derivatives via the β-hydroamidation of terminal ynamides and the α-hydroamidation of internal ynamides, respectively. This reaction proceeded through double elimination of vinyl chlorides and double addition of nucleophiles to alkynes. In addition, it features readily available starting materials, mild reaction conditions, a broad substrate scope, a wide functional group tolerance, and an operational convenience.
本文描述了一种有效的碱促进的串联反应，该反应以乙烯基1,1 - 二氯化物和仲磺酰胺为原料，以炔酰胺为关键中间体。该方法分别通过末端炔酰胺的β-氢酰胺化和内炔酰胺的α-氢酰胺化，为制备（）-1,2-二酰胺和芳基1,1-二酰胺衍生物提供了一种简便的方法。该反应通过氯乙烯的双消除和炔烃的双亲核加成进行。此外，该反应具有起始原料易得、反应条件温和、底物范围广、官能团耐受性好以及操作简便等特点。
