Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Org Lett. 2020 Nov 20;22(22):8802-8807. doi: 10.1021/acs.orglett.0c03160. Epub 2020 Oct 13.
The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en route to α-sulfide amides. Mechanistic studies identified activated sulfoxides as promoters of the desired transformation and enabled the extension of the methodology from benzylic to aliphatic amide substrates.
本文描述了在亲电酰胺活化条件下使用亚砜试剂对叔酰胺的直接α-硫化反应。采用方便易得的试剂进行选择性官能化，生成可分离的锍离子，从而生成α-硫化酰胺。机理研究表明，活化亚砜是促进所需转化的促进剂，并使该方法从苄基酰胺底物扩展到脂肪族酰胺底物。
