Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
J Org Chem. 2016 Sep 2;81(17):8035-42. doi: 10.1021/acs.joc.6b01421. Epub 2016 Aug 10.
An intermolecular alkylation of sulfonamides with trichloroacetimidates is reported. This transformation does not require an exogenous acid, base, or transition metal catalyst; instead the addition occurs in refluxing toluene without additives. The sulfonamide alkylation partner appears to be only limited by sterics, with unsubstituted sulfonamides providing better yields than more encumbered N-alkyl sulfonamides. The trichloroacetimidate alkylating agent must be a stable cation precursor for the substitution reaction to proceed under these conditions.
本文报道了三氯乙腈酸酯与磺酰胺之间的分子间烷基化反应。该转化过程不需要外加酸、碱或过渡金属催化剂，而是在没有添加剂的情况下回流甲苯中进行。磺酰胺的烷基化伙伴似乎只受空间位阻的限制，取代反应中未取代的磺酰胺比更具阻碍性的 N-烷基磺酰胺提供更好的产率。在这些条件下，三氯乙腈酸酯烷基化试剂必须是稳定的阳离子前体，才能进行取代反应。
