Lu Lingxiang, Wang Yi, Zhang Wendy, Zhang Wen, See Kimberly A, Lin Song
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
J Am Chem Soc. 2023 Oct 18;145(41):22298-22304. doi: 10.1021/jacs.3c06794. Epub 2023 Oct 6.
The cross-electrophile dialkylation of alkenes enables the formation of two C(sp)-C(sp) bonds from readily available starting materials in a single transformation, thereby providing a modular and expedient approach to building structural complexity in organic synthesis. Herein, we exploit the disparate electronic and steric properties of alkyl halides with varying degrees of substitution to accomplish their selective activation and addition to alkenes under electrochemical conditions. This method enables regioselective dialkylation of alkenes without the use of a transition-metal catalyst and provides access to a diverse range of synthetically useful compounds.
烯烃的交叉亲电二烷基化反应能够通过单一转化,从容易获得的起始原料形成两个C(sp)-C(sp)键,从而为有机合成中构建结构复杂性提供了一种模块化且便捷的方法。在此,我们利用不同取代程度的卤代烃的不同电子和空间性质,在电化学条件下实现它们的选择性活化并加成到烯烃上。该方法能够在不使用过渡金属催化剂的情况下实现烯烃的区域选择性二烷基化反应,并可用于合成多种具有合成价值的化合物。