Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4738-4748.DOI: 10.6023/cjoc202110010 Previous Articles     Next Articles

ARTICLES

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a,*(), 刘燕a, 葛元元a, 董少轩a, 宋赛依a, 杨亮茹a,*(), 肖咏梅a, 张守仁b,*(), 屈凌波c,*()   

  1. 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 发布日期:2021-11-17
  • 通讯作者: 袁金伟, 杨亮茹, 张守仁, 屈凌波
  • 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)

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

Jinwei Yuana(), Yan Liua, Yuanyuan Gea, Shaoxuan Donga, Saiyi Songa, Liangru Yanga(), Yongmei Xiaoa, Shouren Zhangb(), Lingbo Quc()   

  1. 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
  • Received:2021-10-09 Revised:2021-11-09 Published:2021-11-17
  • Contact: Jinwei Yuan, Liangru Yang, Shouren Zhang, Lingbo Qu
  • 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)

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