The catalytic use of a sodium amide has been exploited for formal allylic C(sp3)-H bond activation of alkenes under mild conditions. Subsequent C-C bond formations with imines have proceeded in high yields with complete regioselectivity and excellent geometric selectivity. Aromatic cyano, chloro, and bromo functionalities are tolerated by the transition metal-free catalyst. Complex amines bearing a C═C double bond and distinct heteroaromatic units have been prepared in a single step. The critical importance of sodium versus other s-, p-, d-, and f-block metals as well as metal-free systems has been revealed. In addition, two catalytically active sodium-based intermediates were detected by NMR and HRMS analyses.

中文翻译：

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由酰胺钠引发的烯烃的形式烯丙基 C(sp3)-H 键活化

氨基钠的催化用途已被用于在温和条件下烯烃的正式烯丙基 C(sp3)-H 键活化。随后与亚胺的 CC 键形成以高产率进行，具有完全的区域选择性和优异的几何选择性。不含过渡金属的催化剂可耐受芳香族氰基、氯和溴官能团。带有 C=C 双键和不同杂芳族单元的复合胺已在一个步骤中制备。钠相对于其他 s-、p-、d- 和 f-嵌段金属以及无金属系统的关键重要性已被揭示。此外，通过 NMR 和 HRMS 分析检测到两种具有催化活性的钠基中间体。