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Hydroalkylation of styrenes enabled by boryl radical mediated halogen atom transfer
Chemical Science ( IF 8.4 ) Pub Date : 2024-05-03 , DOI: 10.1039/d4sc01731e
Serena Pillitteri 1 , Rajat Walia 2, 3 , Erik V. Van der Eycken 1, 4 , Upendra K. Sharma 1
Affiliation  

In this study, we present an inexpensive, stable, and easily available boryl radical source (BPh4Na) employed in a Halogen Atom Transfer (XAT) methodology. This mild and convenient strategy unlocks the use of not only alkyl iodides as radical precursors but also of the more challenging alkyl and aryl bromides to generate C-centered radicals. The generated radicals were further engaged in the anti-Markovnikov hydroalkylation of electronically diverse styrenes, therefore achieving the formation of C(sp3)–C(sp3) and C(sp3)–C(sp2) bonds. A series of experimental and computational studies revealed the prominent role of BPh4Na in the halogen abstraction step.

中文翻译:

通过硼基自由基介导的卤素原子转移实现苯乙烯的加氢烷基化

在这项研究中,我们提出了一种用于卤素原子转移(XAT)方法的廉价、稳定且易于获得的硼基自由基源(BPh 4 Na)。这种温和而方便的策略不仅可以使用烷基碘作为自由基前体,还可以使用更具挑战性的烷基溴和芳基溴来产生以碳为中心的自由基。产生的自由基进一步参与电子多样化苯乙烯的马尔可夫尼科夫加氢烷基化,从而形成C(sp 3 )–C(sp 3 )和C(sp 3 )–C(sp 2 )键。一系列实验和计算研究揭示了 BPh 4 Na 在卤素提取步骤中的重要作用。
更新日期:2024-05-03
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