烯烃与乙腈的α-C(sp(3))-H键发生的涉及1,2-芳基迁移的氧化自由基1,2-烷基芳基化反应。
Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration.
作者信息
Li Yang, Liu Bang, Li Hai-Bing, Wang Qiuan, Li Jin-Heng
机构信息
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
出版信息
Chem Commun (Camb). 2015 Jan 21;51(6):1024-6. doi: 10.1039/c4cc08902b.
A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp(3))-H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with acetonitriles, giving 5-oxo-pentanenitriles in good to excellent yields. This method proceeds via the C(sp(3))-H oxidative coupling with the C-C double bond and 1,2-aryl-migration, and represents a new access to acyclic molecules through metal-free oxidative alkene 1,2-alkylarylation.
本文报道了一种新颖的无金属氧化反应，即未活化烯烃与乙腈的α-C(sp(3))-H键进行1,2-烷基芳基化反应，用于合成5-氧代戊腈。在过氧苯甲酸叔丁酯（TBPB）存在下，多种α-芳基烯丙醇与乙腈发生1,2-烷基芳基化反应，以良好至优异的产率得到5-氧代戊腈。该方法通过C(sp(3))-H与C-C双键的氧化偶联以及1,2-芳基迁移进行，代表了一种通过无金属氧化烯烃1,2-烷基芳基化获得非环状分子的新途径。
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