Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
Department of Chemistry, Wroclaw University , F. Joliot-Curie 14, Wroclaw 50-383, Poland.
Org Lett. 2017 Sep 1;19(17):4656-4659. doi: 10.1021/acs.orglett.7b02288. Epub 2017 Aug 22.
Despite recent progress in catalytic cross-coupling technologies, the direct activation of N-alkyl-N-aryl amides has been a challenging transformation. Here, we report the first Suzuki cross-coupling of N-methylamino pyrimidyl amides (MAPA) enabled by the controlled n → π conjugation and the resulting remodeling of the partial double bond character of the amide bond. The new mode of amide activation is suitable for generating acyl-metal intermediates from unactivated primary and secondary amides.
尽管近年来催化交叉偶联技术取得了进展，但 N-烷基-N-芳基酰胺的直接活化仍然是一项具有挑战性的转化。在这里，我们报告了首例通过控制 n → π 共轭和酰胺键部分双键性质的重塑来实现 N-甲基氨基嘧啶酰胺 (MAPA) 的铃木交叉偶联。这种新的酰胺活化模式适用于从未活化的伯酰胺和仲酰胺生成酰基金属中间体。
