Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2116-2120.DOI: 10.6023/cjoc202010008 Previous Articles     Next Articles



梁静茹1, 王冰莹1, 黄成尹1, 叶晓君1, 温燕梅1,*()   

  1. 1 广东海洋大学化学与环境学院 广东湛江 524088
  • 收稿日期:2020-10-07 修回日期:2020-12-16 发布日期:2021-02-07
  • 通讯作者: 温燕梅
  • 作者简介:
    † 共同第一作者
  • 基金资助:
    广东海洋大学创新强校工程(230419054); 广东海洋大学大学生创新训练(580520106); 广东海洋大学学位与研究生教育改革研究(521002082)

Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by One-Pot Method

Jingru Liang1, Bingying Wang1, Chengyin Huang1, Xiaojun Ye1, Yanmei Wen1,*()   

  1. 1 Faculty of Chemistry and Environmental Science, Guangdong Ocean University, Zhanjiang, Guangdong 524088
  • Received:2020-10-07 Revised:2020-12-16 Published:2021-02-07
  • Contact: Yanmei Wen
  • About author:
    * Corresponding author. E-mail:
    † These authors contributed equally to this work
  • Supported by:
    Project of Enhancing School with Innovation of Guangdong Ocean University(230419054); College Students Innovation Program of Guangdong Ocean University(580520106); Graduate Education Innovation Program of Guangdong Ocean University(521002082)

1,3-Conjugated olefins are very useful synthetic intermediates. Furthermore, 1,3-diene moiety is an important unit often found in many polymers, natural products and biologically active compounds. For these reasons, the design and synthesis of compounds containing a diene moiety have received considerable attention in organic synthesis and have been extensively studied. Among these methods, the Heck cross-coupling reaction between alkenyl halide and terminal alkene under palladium catalysis has become a powerful tool for the synthesis of dienes. Recently, many research groups have focused on “one-pot method” cascade reactions to form carbon-carbon bond due to not only their convenient and simple operation, but also their high atomic economy. Using terminal alkyne and bis(pinacolato)diboron as starting materials and NaOMe as the base, alkenyl borates were formed, and a series of 1,3-butadienes were directly synthesized via palladium-catalyzed homocoupling reaction of alkenyl borates. The structures of all the compounds were confirmed by 1H NMR and 13C NMR. This one pot method is simple and mild, which provides a simple way for the synthesis of a series of 1,3-butadienes.

Key words: one-pot method, terminal alkyne, alkenyl borate, 1,3-butadiene