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2020 , Vol. 40 >Issue 10: 3390 - 3398

DOI: https://doi.org/10.6023/cjoc202004044

研究论文

银催化炔烃与有机高价碘(III)试剂的立体选择性加成反应

  • 陈新宇 ,
  • 刘雪艳 ,
  • 马方 ,
  • 洪先芳 ,
  • 李洪基
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  • 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

  网络出版日期: 2020-07-01

基金资助

国家自然科学基金（No.21772061）和安徽省高校自然科学基金（No.KJ2017A388）资助项目.

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

  • Chen Xinyu ,
  • Liu Xueyan ,
  • Ma Fang ,
  • Hong Xianfang ,
  • Li Hongji
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  • 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 date: 2020-04-27

  Revised date: 2020-06-23

  Online 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).

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摘要

报道了一种银催化功能化炔烃与有机高价碘（Ⅲ）试剂的立体选择性加成反应.该反应体系底物适用范围广，可以中等到优秀的收率得到烯基酯类化合物.分子内的控制实验证实，有机高价碘试剂分子中的芳基显著促进与其相连的I—O键优先断裂，进而参与后续的立体选择性加成反应.

关键词： 银催化; 炔烃; 高价碘(III)试剂; 立体选择性加成

本文引用格式

陈新宇 , 刘雪艳 , 马方 , 洪先芳 , 李洪基 . 银催化炔烃与有机高价碘(III)试剂的立体选择性加成反应[J]. 有机化学, 2020 , 40(10) : 3390 -3398 . DOI: 10.6023/cjoc202004044

Abstract

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

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