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2021 , Vol. 41 >Issue 12: 4738 - 4748

DOI: https://doi.org/10.6023/cjoc202110010

研究论文

光催化下β-萘酚与二芳基膦氧化物区域选择性邻位膦酰化研究

  • 袁金伟 ,
  • 刘燕 ,
  • 葛元元 ,
  • 董少轩 ,
  • 宋赛依 ,
  • 杨亮茹 ,
  • 肖咏梅 ,
  • 张守仁 ,
  • 屈凌波
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  • a 河南工业大学化学化工学院 郑州 450001
    b 黄河科技学院纳米功能材料研究所 郑州 450006
    c 郑州大学化学学院 郑州 450001

收稿日期: 2021-10-09

  修回日期: 2021-11-09

  网络出版日期: 2021-11-17

基金资助

河南省教育厅自然科学基金(21A150016); 河南工业大学创新基金支持计划专项(2020ZKCJ29); 河南工业大学省高校创新基金(2017RCJH08); 河南省高校国家大学生创新(201910463009); 河南省高校国家大学生创新(201910463013)

收起

Visible-Light-Induced Regioselective ortho-C—H Phosphonylation of β-Naphthols with Diarylphosphine Oxides

  • Jinwei Yuan ,
  • Yan Liu ,
  • Yuanyuan Ge ,
  • Shaoxuan Dong ,
  • Saiyi Song ,
  • Liangru Yang ,
  • Yongmei Xiao ,
  • Shouren Zhang ,
  • Lingbo Qu
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  • a School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001
    b Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006
    c College of Chemistry, Zhengzhou University, Zhengzhou 450001
* Corresponding authors. E-mail: ;
;
;

Received date: 2021-10-09

  Revised date: 2021-11-09

  Online published: 2021-11-17

Supported by

Natural Science Foundation in Department of Education of Henan Province(21A150016); Innovative Funds Plan of Henan University of Technology(2020ZKCJ29); Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology(2017RCJH08); National Undergraduate Innovation and Entrepreneurship Training Program from the University in Henan Province(201910463009); National Undergraduate Innovation and Entrepreneurship Training Program from the University in Henan Province(201910463013)

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摘要

以荧光素为有机光催化剂, K2S2O8为氧化剂, 在室温氮气保护下研究了β-萘酚与二芳基氧化膦的区域选择性邻位C—H膦酰化反应. 该反应条件温和, 官能团适用范围广, 产率高, 区域选择性好, 是β-萘酚改性的理想而实用的选择. 实验结果揭示反应通过自由基途径进行.

关键词： β-萘酚; 二芳基膦氧化物; 光催化; 膦酰化; 自由基反应

本文引用格式

袁金伟 , 刘燕 , 葛元元 , 董少轩 , 宋赛依 , 杨亮茹 , 肖咏梅 , 张守仁 , 屈凌波 . 光催化下β-萘酚与二芳基膦氧化物区域选择性邻位膦酰化研究[J]. 有机化学, 2021 , 41(12) : 4738 -4748 . DOI: 10.6023/cjoc202110010

Abstract

A metal-free visible-light-induced regioselective ortho-C—H phosphonylation of β-naphthols with diarylphosphine oxides has been developed using fluorescein as an organophotoredox catalyst in the presence of K2S2O8 at room temperature under N2 atmosphere. This feature along with mild reaction conditions, sensitive functional group tolerance, good to excellent yields, high regioselectivity, and scale-up synthesis makes it an ideal and practical alternative modification of β-naphthols. The experimental result suggests that a radical pathway is involved in the reaction.

Key words： β-naphthols; diarylphosphine oxide; visible-light catalysis; phosphonylation; radical reaction

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