Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3390-3398.DOI: 10.6023/cjoc202004044 Previous Articles     Next Articles

Special Issue: 黄乃正院士七十华诞专辑


陈新宇a, 刘雪艳b, 马方a, 洪先芳a, 李洪基a   

  1. a 淮北师范大学化学与材料科学学院 教育部绿色和精准合成化学及应用重点实验室 安徽淮北 235000;
    b 蚌埠产品质量监督检验研究院 安徽蚌埠 233040
  • 收稿日期:2020-04-27 修回日期:2020-06-23 发布日期:2020-07-01
  • 通讯作者: 李洪基
  • 基金资助:

Silver-Catalyzed Stereoselective Addition of Organic Hypervalent Iodine(III) Reagents to Alkynes

Chen Xinyua, Liu Xueyanb, Ma Fanga, Hong Xianfanga, Li Hongjia   

  1. a Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education, School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000;
    b Bengbu Product Quality and Inspection Institute, Bengbu, Anhui 233040
  • Received:2020-04-27 Revised:2020-06-23 Published:2020-07-01
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21772061) and the Natural Science Foundation for the Higher Education Institutions of Anhui Province (No. KJ2017A388).

A silver-catalyzed stereoselective addition reaction of functionalized alkynes with organic hypervalent iodine(Ⅲ) reagents as nucleophiles is reported, providing an approach to vinyl esters in high yields with excellent group tolerance. Intramolecular experiment demonstrates that the presence of aryl group considerably affects the cleavage of I-O bond within hypervalent iodine(Ⅲ) reagents, which is also responsible for the high stereoeselectivity observed in this catalytic system.

Key words: silver catalysis, alkyne, hypervalent(III) iodine reagent, stereoselective addition