Donor‐Acceptor Substituted 2‐Phenylpyridines by Means of Reductive C,C–Cross Coupling Reaction
Donor‐Acceptor Substituted 2‐Phenylpyridines by Means of Reductive C,C–Cross Coupling Reaction
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DOI：
10.1002/slct.201600707
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发表时间：
2016-08
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影响因子：
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通讯作者：
Sebastian Triller;Tim Dittmann;M. Bendig;Jan Schnelle;Tom Friedmann;J. Heck
中科院分区：
文献类型：
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作者：
Sebastian Triller;Tim Dittmann;M. Bendig;Jan Schnelle;Tom Friedmann;J. Heck
利用Gosmini等人开发的还原性镍催化的C，C-交叉偶联反应制备了具有潜在的诱导二次谐波产生能力的2-苯基吡啶类化合物。我们成功地从供体官能化的芳基卤化物和受体修饰的2-卤代吡啶直接获得了所需的2-苯基吡啶，使用廉价且易于制备的Ni催化剂。结果表明，在该反应中甚至容许羟基和羧酸的存在，而在含甲酰基的吡啶底物的情况下，没有获得C，C-偶联产物。然而，偶联是成功的，当甲酰基功能保护的缩醛形成。
The preparation of 2-phenylpyridines decorated with an electron donating and accepting unit, which are potentially suitable to induce second harmonic generation, was performed by means of reductive nickel catalyzed C,C-cross coupling reaction, developed by Gosmini et. al. We were successful to obtain the desired 2-phenylpyridines directly from donor-functionalized arylhalides and acceptor-modified 2-halopyridines with a cheap and easy to prepare Ni catalyst. It turned out that even the presence of hydroxy groups and carboxylic acids are tolerated in this reaction, whereas in the case of a formyl group containing pyridine substrate no C,C-coupled product was obtained. However, the coupling was successful when the formyl function was protected by an acetal formation.