Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1987-1997.DOI: 10.6023/cjoc202312023 Previous Articles     Next Articles

ARTICLES

四丁基三溴化铵促进的有机硼酸在无过渡金属条件下的脱硼硒化、溴化和羟基化反应

田永盛a, 魏斓枫c, 黄嘉为a, 韦玉a, 徐亮a,*(), 刘帅b,*()   

  1. a 石河子大学化学化工学院/化工绿色过程省部共建国家重点实验室培育基地 新疆石河子 832003
    b 石河子大学兵团能源发展研究院 新疆石河子 832003
    c 新疆工程学院新疆煤矿灾害智能防控与应急重点实验室 乌鲁木齐 830023
  • 收稿日期:2023-12-24 修回日期:2024-01-17 发布日期:2024-02-19
  • 基金资助:
    国家自然科学基金(22061036); 国家自然科学基金(21963010)

Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions

Yongsheng Tiana, Lanfeng Weic, Jiawei Huanga, Yu Weia, Liang Xua,*(), Shuai Liub,*()   

  1. a School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Enginering, Shihezi University, Shihezi, Xinjiang 832003
    b Bintuan Energy Development Institute, Shihezi University, Shihezi, Xinjiang 832003
    c Xinjiang Key Laboratory of Coal Mine Disasters Intelligent Prevention and Emergency Response, Xinjiang Institute of Engineering, Urumqi 830023
  • Received:2023-12-24 Revised:2024-01-17 Published:2024-02-19
  • Contact: * xuliang4423@shzu.edu.cn; liushuai0053@shzu.edu.cn
  • Supported by:
    National Natural Science Foundation of China(22061036); National Natural Science Foundation of China(21963010)

Divergent approaches for the convenient ipso-functionalization of organic boronic acids are presented, capitalizing on tetrabutylammonium tribromide (TBATB) under different, yet transition metal-free conditions. Through these methods, a wide array of organoborons can be efficiently converted into their corresponding selenylated, brominated, or hydroxylated products in moderate to excellent yields. The versatility of this strategy lies in its transition metal-free conditions, simple operation, and step-economic pathways, offering a promising idea for the ipso-functionalization of organoborons

Key words: tetrabutylammonium tribromide, organic boronic acid, selenylation, bromination, hydroxylation, transition metal-free