N-alkyl Indazoles are highly privileged skeleton in pharmaceutical applications. Generally, N1 and N2-alkyl indazoles represents distinct pharmaceutical and biological activities due to their molecular shape and electrostatic distribution. Herein, we described a regiodivergent N-alkylation of indazoles via nucleophilic ring opening of D-A cyclopropanes by employing different Lewis acid catalysts. Under the catalysis of Al(OTf)3, kinetic controlled N2-alkyl indazoles were achieved, while Co(NTf2)2 facilitated the formation of N1-alkyl indazoles. The methodology exhibited a broad substrate scope, affording the corresponding N1 and N2 alkylation products selectively in high yields with good to excellent regioselectivities.

中文翻译：

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路易斯酸催化吲哚唑与供体-受体环丙烷的区域性差异 N-烷基化反应


N-烷基吲哚唑是制药应用中极具特权的骨架。通常，N1 和 N2-烷基吲哚唑因其分子形状和静电分布而代表不同的药物和生物活性。在本文中，我们描述了通过使用不同的路易斯酸催化剂通过 D-A 环丙烷的亲核开环对吲哚唑的区域发散 N-烷基化反应。在 Al（OTf）3 的催化下，实现了动力学控制的 N2-烷基吲哚唑，而 Co（NTf2）2 促进了 N1-烷基吲哚唑的形成。该方法表现出广泛的底物范围，以高产率选择性地提供相应的 N1 和 N2 烷基化产物，具有良好至优异的区域选择性。