Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2545-2551.DOI: 10.6023/cjoc201506025 Previous Articles     Next Articles



温运明, 陈桂芳, 唐渝, 陈静, 杨骏, 张渊明   

  1. 暨南大学化学系 广州 510632
  • 收稿日期:2015-06-18 修回日期:2015-08-25 发布日期:2015-08-31
  • 通讯作者: 唐渝, 张渊明;
  • 基金资助:

    国家自然科学基金(No. 21276104)资助项目.

Effective Bismuth(III)-Promoted Barbier-Grignard-Type Reactions of Bromides with Aldehydes

Wen Yunming, Chen Guifang, Tang Yu, Chen Jing, Yang Jun, Zhang Yuanming   

  1. Department of Chemistry, Jinan University, Guangzhou 510632
  • Received:2015-06-18 Revised:2015-08-25 Published:2015-08-31
  • Supported by:

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

A highly versatile and efficient method has been developed for the Barbier-Grignard-type arylation and alkylation of aldehydes using unactivated bromides and Mg in tetrahydrofuran at 65 ℃ promoted by BiCl3 and PPh3. This method has offered high yields of 61%~99% mostly, mild reaction conditions, short reaction time, easy workup and a one-pot procedure. The steric, electronic effects and some new results have been discussed. A possible mechanism catalyzed by BiCl3 and Ph3P was reasonably proposed.

Key words: secondary alcohol, Barbier-Grignard-type reaction, one-pot, aldehyde, BiCl3