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含氟脯氨酸类配体在亨利反应中的应用

万力1,蔡春1,2*   

  1. (1.南京理工大学化工学院 南京 210094;2.中国科学院上海有机氟化学重点实验室 上海 200032)
  • 收稿日期:2011-03-25 修回日期:2011-05-16 出版日期:2012-02-10 发布日期:2012-02-10
  • 通讯作者: 蔡春，教授; Tel:025-84315514; Fax:025-84315030; E-mail:c.cai@mail.njust.edu.cn; 研究方向：精细有机化学品合成
  • 基金资助:
    南京理工大学自主科研基金(2010ZDJH14)资助项目

Synthesis and Application of A Fluorous Proline-derived Ligand in the Copper(Ⅱ)-catalyzed Henry Reaction

WAN Li1, CAI Chun1,2*   

  1. (1.Chemical Engineering College,Nanjing University of Science & Technology,Nanjing 210094;
    2.Key Laboratory of Organofluorine Chemistry,Shanghai Institute of
    Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032)
  • Received:2011-03-25 Revised:2011-05-16 Published:2012-02-10 Online:2012-02-10
  • Contact: Chun Cai

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摘要： 以脯氨酸为前体，设计并合成了一种新的含氟配体，并将其应用到铜催化的亨利反应中。 以硝基甲烷和对硝基苯甲醛的反应为模板反应，考察了配体、铜源、溶剂和碱对反应收率的影响，对反应条件进行了优化。 以含氟脯氨酸衍生物为配体，乙酸铜为铜源，甲醇作溶剂，三乙胺作为碱，不同取代基的芳香醛和硝基烷烃在室温下反应，得到53%～98%的收率。

关键词: &, beta, -硝基醇, 亨利反应, 含氟脯氨酸配体, 铜催化剂

Abstract: A new fluorous proline-derived ligand has been synthesized and applied to the copper-catalyzed Henry reaction. The reaction conditions were optimized in terms of ligand, Cu source, solvent and base taking the reaction of 4-nitrobenzaldehyde and nitromethane as a model reaction. The optimized conditions are:using fluorous proline imide as ligand, copper acetate as copper source, methanol as solvent and triethylamine as base and the reaction was carried out at room temperature. A wide range of substrates were investigated under the optimized conditions and the yields of the target products varied from 53% to 98%.

Key words: &, beta, -niroalcohols, Henry reaction, fluorous proline ligand, copper catalyst

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