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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (9): 1655-1659. 上一篇    下一篇

研究简报

氟喹诺酮作为钯催化Heck反应有效配体的研究

伍 强a; 王 磊*,a,b   

  1. (a淮北煤炭师范学院化学系 淮北 235000)
    (b中国科学院上海有机化学研究所金属有机化学国家重点实验室 上海 200032)
  • 收稿日期:2008-03-27 修回日期:2008-04-14 发布日期:2008-09-20
  • 通讯作者: 王 磊

Fluoroquinolones as Effective Ligands for Palladium Catalyzed Heck Reactions

WU, Qianga; WANG, Lei*,a,b   

  1. (a Department of Chemistry, Huaibei Coal Teachers College, Huaibei 235000)
    (b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry,
    Chinese Academy of Sciences, Shanghai 200032)
  • Received:2008-03-27 Revised:2008-04-14 Published:2008-09-20
  • Contact: WANG, Lei

PDF

1366

被引次数

21

研究了氟喹诺酮作为钯催化Heck反应的有效配体. 碘苯、溴苯和其它芳基卤衍生物与丙烯酸丁酯、苯乙烯等取代乙烯类化合物在钯和氟喹诺酮的催化下发生Heck反应. 讨论了配体、催化剂用量、碱和溶剂对Heck反应产率的影响. 该反应的最优化条件是: 钯源为Pd(OAc)2 (0.1 mol%), 诺氟沙星作为配体(0.2 mol%), K2CO3作为碱, DMA作为溶剂, 取代碘苯及溴苯和它们的衍生物与丙烯酸丁酯、苯乙烯等乙烯基化合物的反应均可以得到高收率的目标偶联产物.

关键词: 氟喹诺酮, Pd催化剂, Heck反应

Some fluoroquinolones were found to be the highly efficient ligands for Heck reaction. Iodobenzene, bromobenzene and their derivatives reacted smoothly with n-butyl acrylate or styrene under phosphine-free reaction conditions in the presence of palladium acetate and fluoroquinolones. The effect of ligands, amount of catalyst, bases and solvent on the yield of the desired product was studied by using the reaction of 4-bromobenzonitrile with n-butyl acrylate as a model reaction. The results showed that the optimized reaction condition involved norfloxacin (0.2 mol%) as ligand, Pd(OAc)2 (0.1 mol%) as palladium source, K2CO3 as base, and DMA as solvent. For the reactions of aryl iodides and bromides with n-butyl acrylate or styrene, good to excellent yields of the corresponding Heck reaction products were obtained under the optimized reaction conditions.

Key words: fluoroquinolone, Heck reaction, Pd catalyst