Transition metal-catalyzed cross coupling with N-acyliminium ions derived from quinolines and isoquinolines
Transition metal-catalyzed cross coupling with N-acyliminium ions derived from quinolines and isoquinolines
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DOI：
10.1039/c1sc00026h
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发表时间：
2011-01-01
期刊：
影响因子：
8.4
通讯作者：
Doyle, Abigail G.
中科院分区：
文献类型：
--
作者：
Graham, Thomas J. A.;Shields, Jason D.;Doyle, Abigail G.
Ni（0）催化剂有助于在宽范围的p-中性和p-缺乏的芳基硼酸与衍生自喹啉和异喹啉的N-酰基硼酸前体之间有效地形成C-C键。该反应在温和的条件下进行，并且耐受常见的有机官能团。此外，一个简单的一锅协议适合直接使用取代的喹啉。与初步数据一致，揭示了一个温和的，有机硼酸盐介导的对映体富集的N-酰基前体的外消旋化，初步结果表明，手性亚磷酰胺连接的镍催化剂促进外消旋底物的对映体选择性芳基化，没有证据表明在催化过程中的动力学分辨率。
A Ni(0) catalyst facilitates efficient C-C bond formation between a wide range of p-neutral and p-deficient aryl boronic acids and N-acyliminium precursors derived from quinoline and isoquinoline. The reaction proceeds under mild conditions and is tolerant of common organic functional groups. In addition, a simple one-pot protocol amenable to the direct use of substituted quinolines is described. Consistent with preliminary data revealing a mild, organoboronate-mediated racemization of enantioenriched N-acyliminium precursors, initial results indicate that a chiral phosphoramidite-ligated nickel catalyst promotes enantioselective arylation of racemic substrate with no evidence of a kinetic resolution during catalysis.