Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1957-1967.DOI: 10.6023/cjoc202103041 Previous Articles     Next Articles

Special Issue: 热点论文虚拟合集



黄云帅1, 靳小慧1, 张凤莲1,*(), 汪义丰1,*()   

  1. 1 中国科学技术大学化学系 合肥 230026
  • 收稿日期:2021-03-23 修回日期:2021-04-09 发布日期:2021-04-25
  • 通讯作者: 张凤莲, 汪义丰
  • 基金资助:
    国家自然科学基金(21971226); 中央高校基本科研业务费专项资金(WK2060000017)

4-Dimethylaminopyridine-Boryl Radical Promoted Regioselective Radical Hydroboration of Electron-Deficient Alkenes

Yunshuai Huang1, Xiaohui Jin1, Fenglian Zhang1,*(), Yifeng Wang1,*()   

  1. 1 Department of Chemistry, University of Science and Technology of China, Hefei 230026
  • Received:2021-03-23 Revised:2021-04-09 Published:2021-04-25
  • Contact: Fenglian Zhang, Yifeng Wang
  • About author:
    * Corresponding authors. E-mail: ;
  • Supported by:
    National Natural Science Foundation of China(21971226); Fundamental Research Funds for the Central Universities(WK2060000017)

Organoboron compounds have shown significant applications in modern chemical synthesis. Hydroboration of alkenes is among the most widely used methods to access these targets. Herein, a regioselective radical hydroboration reaction of electron-deficient alkenes with 4-dimethylaminopyridine (DMAP)-boryl radical for the synthesis of α-boryl functionalized molecules is reported. The reaction features specific α-regioselectivity, mild reaction conditions, good functional group tolerance, and broad substrate scope. α,β-Unsaturated esters, amides, carboxylic acid, nitrile, trifluoromethyl molecule, sulfone, and phosphonate are viable substrates for this reaction. The resulting α-boryl functionalized molecules can be further transformed to various useful building blocks.

Key words: 4-dimethylaminopyridine-boryl radical, electron-deficient alkenes, regioselectivity, hydroboration, radical chemistry