Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2419-2425.DOI: 10.6023/cjoc202003038 Previous Articles     Next Articles

银催化1-溴代炔烃的功能化反应:高区域和立体选择性合成(Z)-β-溴-1-芳基乙烯基芳基酯

孙明利a,b, 张家俊a,d, 张义成a,c, 李品华a,c, 王磊a,b,c   

  1. a 淮北师范大学化学与材料科学学院 安徽淮北 235000;
    b 台州学院医药化工与材料工程学院 浙江台州 318000;
    c 中国科学院上海有机化学研究所金属有机国家重点实验室 上海 200032;
    d 浙江金华康恩贝生物药业有限公司 浙江金华 321016
  • 收稿日期:2020-03-15 修回日期:2020-05-18 出版日期:2020-08-25 发布日期:2020-05-29
  • 通讯作者: 张义成, 王磊 E-mail:lbqzhych@163.com;leiwang@chnu.edu.cn
  • 基金资助:
    国家自然科学基金(No.21772062)资助项目.

A Silver-Catalyzed Functionalization of 1-Bromoalkynes: Highly Regio-and Stereo-selective Synthesis of (Z)-β-Bromo-1-arylvinyl Aryl Esters

Sun Minglia,b, Zhang Jiajuna,d, Zhang Yichenga,c, Li Pinhuaa,c, Wang Leia,b,c   

  1. a Key Laboratory of Green and Precise Synthetic Chemistry, Ministry of Education, Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000;
    b Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang 318000;
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032;
    c Zhejiang Jinhua CONBA Bio-Pharm. Co., Ltd., Jinhua, Zhejiang 321016
  • Received:2020-03-15 Revised:2020-05-18 Online:2020-08-25 Published:2020-05-29
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21772062).

A silver-catalyzed functionalization of 1-bromoalkynes for the highly regio-and stereo-selective synthesis of (Z)-β-bromo-1-arylvinyl aryl esters was developed. In the presence of Ag2O as a catalyst, and Et3N as a base, the reactions of 1-bromoalkynes with commercially available aromatic carboxylic acids underwent smoothly to afford the corresponding (Z)-β-bromo-1-arylvinyl aryl esters in good yields. The investigation indicates that Ag2O plays an important role in the reaction.

Key words: 1-bromoalkynes, (Z)-β-bromo-1-arylvinyl aryl esters, silver catalysis, regio-selectivity, stereo-selectivity