Mild chlorodifluoroacylation of indoles via self-activation of sodium chlorodifluoroacetate.
Mild chlorodifluoroacylation of indoles via self-activation of sodium chlorodifluoroacetate.
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DOI：
10.1021/ol501854q
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发表时间：
2014-07
期刊：
影响因子：
5.2
通讯作者：
T. Williams;M. Greaney
中科院分区：
文献类型：
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作者：
T. Williams;M. Greaney
报道了用氯二氟乙酸钠（SCDA）对n -烷基酮进行轻度酰化反应，以合成有用的氯二氟酮。羧酸盐的Friedel-Crafts反应性是不寻常的，在类似的缺电子的乙酸盐如三氟乙酸钠中没有观察到。机理实验表明，SCDA特有的生成二氟烃的能力是通过自活化形成活性酯的反应途径的原因。
A mild acylation of N-alkylindoles is reported using sodium chlorodifluoroacetate (SCDA) to synthesize useful chlorodifluoroketones. Friedel-Crafts reactivity of carboxylate salts is unusual and is not observed in similar electron-deficient acetate salts such as sodium trifluoroacetate. Mechanistic experiments indicate that the characteristic ability of SCDA to generate difluorocarbene is responsible for the reaction pathway via self-activation to form the active ester.