Efficient Synthesis of Diaryl Ketones by Nickel-Catalyzed Negishi Cross-Coupling of Amides by Carbon-Nitrogen Bond Cleavage at Room Temperature Accelerated by a Solvent Effect
Efficient Synthesis of Diaryl Ketones by Nickel-Catalyzed Negishi Cross-Coupling of Amides by Carbon-Nitrogen Bond Cleavage at Room Temperature Accelerated by a Solvent Effect
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DOI：
10.1002/chem.201602202
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发表时间：
2016-07-18
影响因子：
4.3
通讯作者：
Szostak, Michal
中科院分区：
文献类型：
--
作者：
Shi, Shicheng;Szostak, Michal
首次报道了酰胺的Negishi交叉偶联反应，在极其温和的条件下，通过选择性活化C-N键合成了多功能的二芳基酮。交叉偶联是用工作台稳定的、廉价的预催化剂[Ni（PPh 3）（2）Cl-2]完成的，该预催化剂显示出高官能团耐受性并能够合成高度官能化的二芳基酮基序。偶联以有利于酮的优异的化学选择性发生（参见联芳基）产物。值得注意的是，该方法代表了迄今为止实现的酰胺N-C键活化的最温和条件（室温，
The first Negishi cross-coupling of amides for the synthesis of versatile diaryl ketones by selective C-N bond activation under exceedingly mild conditions is reported. The cross-coupling was accomplished with bench-stable, inexpensive precatalyst [Ni(PPh3)(2)Cl-2] that shows high functional-group tolerance and enables the synthesis of highly functionalized diaryl ketone motifs. The coupling occurred with excellent chemoselectivity favoring the ketone (cf. biaryl) products. Notably, this process represents the mildest conditions for amide N-C bond activation accomplished to date (room temperature,