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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (03): 368-373. 上一篇    下一篇

研究论文

吡啶氮桥联三唑卡宾反应性质及其Pd(II)-配合物催化杂芳环与芳基溴的α-烷基化反应研究

马亚军*，严彪，郭政科，赵明涛，韩海飞，程芬芬，葛靖国，王金龙，张岗虎   

  1. (榆林学院化学与化工学院 榆林 719000)
  • 收稿日期:2009-11-10 修回日期:2010-08-10 发布日期:2010-10-20
  • 通讯作者: 马亚军 E-mail:mayajun@ylc.net.cn
  • 基金资助:

    国家级.国家自然科学基金

Study on Reactivity of Pyrido-annulated Triazol-3-ylidenes and Its Application of Pd(II) Complex in α-Arylation of Caffeines with Aryl Bromide

MA Ya-Jun, YAN Biao, GUO Zheng-Ke, ZHAO Ming-Tao, HAN Hai-Fei, CHENG Fen-Fen, GE Jing-Guo, WANG Jin-Long, ZHANG Gang-Hu   

  1. (College of Chemistry and Chemical Engineering, Yulin University, Yulin 719000)
  • Received:2009-11-10 Revised:2010-08-10 Published:2010-10-20
  • Contact: 马亚军 MA Ya-Jun E-mail:mayajun@ylc.net.cn

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报道了吡啶氮桥联的双环三唑鎓盐1在NaH, K2CO3为碱的条件下脱去质子, 分别形成三唑卡宾2和卡宾二聚体4, 研究了2和4与亲电试剂的反应性质, 2与水的反应产物3经单晶衍射结构分析. 考察了配体1的卡宾-Pd(II)配合物催化咖啡因与芳基溴的α-芳基化反应, 在优化催化反应条件下, 比较了不同三唑鎓盐之间的催化活性. 结果表明, 三唑鎓盐1表现出优良的催化活性.

关键词: 三唑卡宾, 反应性质, 钯配合物, α-芳基化反应

The carbene 2 and enetetramine 4 were synthesized from the pyrido-annulated triazolium salt 1 by deproton under strong base NaH and weak base K2CO3. The reaction performances of the carbene 2 and its enetetramine 4 with H2O, S8 and Se had also been studied, and the X-ray sin-gle-crystal analysis of the product 3 were studied. Reaction condition effect was tested. The Pd(II) complex of the triazolium carbene 2 turned out to be a powerful catalyst in direct α-arylation of caffeines with aryl bromide, which was comparable with or even superior to other well-established triazolylidenes already in the literature.

Key words: triazolium carbene, reaction property, palladium(II) complex, α-arylation

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