Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2456-2462.DOI: 10.6023/cjoc201602025 Previous Articles     Next Articles

Articles

一种简便高效的Ta2O5催化溴代芳烃和芳酸的Barbier-Grignard反应制备三级醇

王华然, 唐渝, 杨骏, 张渊明   

  1. 暨南大学生命科学技术学院化学系 广州 510632
  • 收稿日期:2016-02-24 修回日期:2016-05-03 发布日期:2016-06-01
  • 通讯作者: 唐渝,E-mail:tytang@jnu.edu.cn;张渊明,E-mail:tzhangym@jnu.edu.cn E-mail:tytang@jnu.edu.cn;tzhangym@jnu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21276104)资助项目.

A Simple and Efficient Synthesis of Tertiary Alcohols via Ta2O5- Catalyzed Barbier-Grignard Addition of Unactivated Aryl Bromides to Aryl Acids

Wang Huaran, Tang Yu, Yang Jun, Zhang Yuanming   

  1. Department of Chemistry, Jinan University, Guangzhou 510632
  • Received:2016-02-24 Revised:2016-05-03 Published:2016-06-01
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21276104).

Carried out in THF-toluene at 103℃, the first one-pot Barbier-Grignard reaction to synthesize tertiary alcohols has been developed and systematically investigated using aromatic acids and unactivated aryl bromides in the presence of 10 mol% of Ta2O5. A wide range of substituted tertiary alcohols were obtained in moderate to good yields of 48%~87%. Steric and electronic effects of reactants on the reaction have been discussed. A possible mechanism catalyzed by Ta2O5 is proposed.

Key words: aryl acid, barbier-grignard-type reaction, synthesis, tertiary alcohol