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咔唑桥连NCN齿形钯配合物催化的唑类C-H键直接芳基化反应
引用本文:宋文越,饶小峰,卜庆青,刘宁.咔唑桥连NCN齿形钯配合物催化的唑类C-H键直接芳基化反应[J].有机化学,2020(2):489-500.
作者姓名:宋文越  饶小峰  卜庆青  刘宁
作者单位:石河子大学化学化工学院新疆兵团绿色化工过程重点实验室;南方科技大学化学系
基金项目:国家自然科学基金(No.U1603103)资助项目.
摘    要:基于咔唑的强给电子能力合成了一种对空气稳定的齿形钯配合物催化剂(C1~C6).这种钯催化剂可高效催化唑类和溴代芳烃的直接芳基化反应,在空气条件下,碳酸钾为碱,无需其他添加剂,即取得了较好的催化活性与底物普适性.在相对温和的条件和催化剂用量为0.5mol%时,即可实现噻唑与溴代芳烃直接芳基化反应顺利进行.值得一提的是,这是目前以KOAc为碱的反应体系中,反应活性最高的催化体系.

关 键 词:咔唑配体  钯配合物  直接芳基化反应  溴代芳烃  偶联反应

Carbazole-Bridged NCN-Pincer Palladium Complex Catalyzed Direct C-H Arylation Reaction of Azoles
Song Wen-Yue,Rao Xiaofeng,Bu Qingqing,Liu Ning.Carbazole-Bridged NCN-Pincer Palladium Complex Catalyzed Direct C-H Arylation Reaction of Azoles[J].Chinese Journal of Organic Chemistry,2020(2):489-500.
Authors:Song Wen-Yue  Rao Xiaofeng  Bu Qingqing  Liu Ning
Institution:(Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan,School of Chemistry and Chemical Engineering,Shihezi University,Shihezi,Xinjiang 832003;Department of Chemistry,Southern University of Science and Technology,Shenzhen,Guangdong 518000)
Abstract:A new type of pincer palladium complexes C1~C6 based on the strong donor strength of carbazoles skeleton were synthesized. The air-and moisture-stable complexes C1~C6 act as efficient catalysts for the direct arylation of azoles with(hetero)aryl bromides in good to excellent yields with broad substrate scope used KOAc as sole base under aerobic conditions. It was demonstrated that this developed protocol was the most catalytic system for the direct C-H bond arylation for thiazoles under relatively mild reaction conditions at a low catalyst loading of 0.5 mol%.
Keywords:carbazole ligand  palladium complex  direct arylation  aryl bromides  coupling reaction
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