甲萘胺衍生物的C-8选择性氧甲酰甲基化反应

Selective C-8 Oxyformyl Methylation of 1-Naphthylamine Derivatives

萘胺类化合物是功能材料和药物中的一种重要芳香化合物,广泛应用于染料和电致发光材料.近年来通过选择性修饰萘胺的母环结构来合成取代萘胺的研究取得了较大进展.本课题组利用双齿螯合基团可以络合稳定过渡金属以促进C-H键官能化且在反应结束后易于去除的特点,发展了钯催化的甲萘胺衍生物的C-8位选择性C-H官能化反应.以氯代乙酸酯为烷基化试剂,以中等产率合成了七个C-8位氧甲酰甲基取代甲萘胺的衍生物,是一种简单方便、绿色环保、选择性好的合成甲萘胺衍生物的新方法.

1-Naphthylamine scaffolds have been widely applied to dyes and electroluminescent materials as an important structural unit.Recently,great development has taken place in the research of selective sitefunctionalization of naphthylamine core for the synthesis of substituted naphthylamine.Our research group reported that the bidentate system would bind tightly to transition-metal catalysts,thereby bringing the catalyst into close proximity to the 8-C-H bond of 1-naphthylamides on the palladium(Ⅱ)-catalyzed quinolinamidedirected regioselective C-8 C-H bond functionalization.We synthesized seven examples of 8-alkylated-1-naphthylamide derivatives in moderate yields for a range of chloroacetates as reagents with this simple,convenient and green synthetic method in good selectivity.