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Ni-catalyzed regioselective hydrobenzylation of alkenes to afford C(sp3)–C(sp3) bonds using BH3 as a reductant
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2022-11-22 , DOI: 10.1039/d2qo01510b
Li Cheng 1, 2 , Quan Lin 1, 2 , Yanhong Song 3 , Hua Chen 3 , Hegui Gong 2 , Yunrong Chen 2
Affiliation  

The nickel-catalyzed reductive olefin hydrocarbonation reaction is one of the powerful tools for the formation of C(sp3)–C bonds. However, the reductive coupling of alkenes with benzyl halides to afford alkyl–benzyl products has rarely been studied using the well-established Ni/SiH methods. Herein, we report a method of Ni-catalyzed regioselective hydrobenzylation of unactivated alkenes to afford anti-Markovnikov products using BH3 as a reductant. This method exhibits good functional group tolerance, a wide scope and high regioselectivity. The mild conditions enable the coupling of terminal and internal alkenes with primary and secondary benzyl halides.

中文翻译:

使用 BH3 作为还原剂,Ni 催化烯烃的区域选择性加氢苄基化以提供 C(sp3)–C(sp3) 键

镍催化的还原性烯烃烃化反应是形成 C(sp 3 )–C 键的有力工具之一。然而,很少使用成熟的 Ni/SiH 方法研究烯烃与苄基卤化物的还原偶联以提供烷基-苄基产物。在此,我们报告了一种使用 BH 3作为还原剂,对未活化的烯烃进行 Ni 催化区域选择性氢化苄化以提供抗马尔可夫尼科夫产物的方法。该方法具有良好的官能团耐受性、广泛的适用范围和高的区域选择性。温和的条件能够使末端和内部烯烃与伯和仲苄基卤化物偶联。
更新日期:2022-11-22
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