通过与氰基胍进行直接亲电芳香取代反应合成苯甲酰胺。
Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine.
作者信息
Naredla Rajasekhar Reddy, Klumpp Douglas A
机构信息
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115.
出版信息
Tetrahedron Lett. 2012 Aug 29;53(35):4779-4781. doi: 10.1016/j.tetlet.2012.06.135.
Abstract
Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Brønsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.
摘要
氰基胍是一种廉价的商品化学品，它被发现是芳烃直接傅克羧酰胺化反应的有用试剂。该反应在过量的布朗斯特超强酸中效果最佳，这一观察结果表明涉及超亲电中间体。理论计算表明，最稳定的双质子化物种涉及胍基和氰基氮原子的质子化。
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