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应用化学 ›› 2011, Vol. 28 ›› Issue (08): 887-891.DOI: 10.3724/SP.J.1095.2011.00541

• 研究论文 • 上一篇    下一篇

醚基化二茂铁基膦配体的合成及其对钯催化的Suzuki偶联反应的促进作用

于宏伟2,3,官旻2,童庆松1,贾莉1,金子林2,施继成1*   

  1. (1.福建师范大学化学与材料学院，福建省高分子材料重点实验室 福州 350007；
    2.大连理工大学,精细化工国家重点实验室 大连；3.石家庄学院化工学院 石家庄)
  • 收稿日期:2010-09-15 修回日期:2010-10-27 出版日期:2011-08-10 发布日期:2011-08-10
  • 通讯作者: 施继成，教授; Tel/Fax:591-83465225; E-mail:jchshi@fjnu.edu.cn; 研究方向：金属有机与络合催化
  • 基金资助:
    国家自然科学基金(20971023)及福建省自然科学基金(2007J0306)资助项目

Synthesis and Enhanced Activity of Etherlized Ferrocenylphosphine for the Palladium-Catalyzed Suzuki Reaction

YU Hongwei2,3, GUAN Min2, TONG Qingsong1, JIA Li1, JIN Zilin2, SHI Jicheng1*   

  1. (1.College of Chemistry and Materials Science,Fujian Key
    Laboratory of Polymer Materials,Fujian Normal University,Fuzhou 350007;
    2.State Key Laboratory of Fine Chemicals,Dalian University of Technology,Dalian;
    3.School of Chemical Engineering,Shijiazhuang College,Shijiazhuang)
  • Received:2010-09-15 Revised:2010-10-27 Published:2011-08-10 Online:2011-08-10

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1696

摘要：

通过乙酸1-(2-二苯膦基二茂铁基)-乙基酯和二甘醇反应，制得新的醚基化的二茂铁基膦配体2-二苯膦基二茂铁基-乙基-5-羟基-3-氧杂戊醚(产率77%)，其结构经1H NMR、13C NMR、31P NMR及MS鉴定。 初步研究发现，该醚基化的二茂铁基膦可作为支持配体应用于钯催化的Suzuki反应中，可催化溴代芳烃及带吸电子基的氯代芳烃与苯基硼酸偶联反应制得相应的联芳烃。 催化反应数据表明，配体中的醚氧与Pd中心的配位作用对提高该Pd催化剂的催化性能有一定贡献。

关键词: 二茂铁膦, 醚化, 钯, Suzuki偶联反应, 联芳烃

Abstract:

A new etherlized ferrocenylphosphine ligand, 2-diphenylphosphino-ferrocenyl-ethyl-5-hydroxyl-3-oxo-pentyl ether, was prepared by the reaction of acetyl 1-(diphenylphosphinoferrocenyl)ethyl ester with diethylene glycol in 77% yield. Its structure was characterized by 1H NMR, 13C NMR, 31P NMR and MS. The synthesized ferrocenylphosphine has been applied as supporting ligand in the palladium-catalyzed Suzuki reaction; its ligated palladium catalyst is effective for coupling a range of aryl bromides as well as aryl chlorides having electron-withdrawing groups with phenylboronic acid to prepare the corresponding biaryls. The possible coordination of ether-oxygen to the Pd center may enhance the catalytic performance of the ligand for cross-coupling reaction.

Key words: ferrocenylphosphine, etherlization, palladium, Suzuki reaction, biaryl

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