A regioselective one‐pot approach to the synthesis of C4‐alkylated tetrahydropyridines (THPs) and tetrahydroquinolines (THQs) by dearomatization of pyridines and quinolines has been developed. The transformation is achieved by the BF₃ ⋅ OEt₂‐mediated, C4‐selective addition of Grignard reagents, followed by a cascade of enamine protonation and the subsequent Et₃SiH reduction of the resulting iminium ions. This protocol not only provides a facile synthetic approach to C4‐substituted THPs and THQs, but also offers a new strategy for the dearomatization of heteroaromatics.

中文翻译：

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C4烷基化的四氢吡啶和四氢喹啉的一锅脱气方法

已开发出一种通过对吡啶和喹啉进行脱芳香化反应来合成C4烷基化的四氢吡啶（THP）和四氢喹啉（THQ）的区域选择性单锅法。该转换是由BF实现₃  ⋅OET ₂介导的，C4-选择性添加格氏试剂，随后质子化烯胺的级联和随后的Et ₃ SiH基减少所得亚胺离子。该协议不仅为C4取代的THP和THQ提供了一种简便的合成方法，而且还为杂芳烃的脱芳香化提供了新的策略。