Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3431-3438.DOI: 10.6023/cjoc202005001 Previous Articles     Next Articles


张红a, 王明扬a, 吴新鑫a, 朱晨a,b   

  1. a 苏州大学材料与化学化工学部 苏州 215123;
    b 中国科学院上海有机化学研究所 天然产物有机合成重点实验室 上海 200032
  • 收稿日期:2020-05-01 修回日期:2020-05-30 发布日期:2020-06-10
  • 通讯作者: 朱晨
  • 基金资助:

Radical-Mediated Bromoalkylation of [1.1.1]propellane: Synthesis of Bromo-substituted Bicyclo[1.1.1]pentane Derivatives

Zhang Honga, Wang Mingyanga, Wu Xinxina, Zhu Chena,b   

  1. a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123;
    b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Shanghai 200032
  • Received:2020-05-01 Revised:2020-05-30 Published:2020-06-10
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21722205, 21971173).

As a bioisostere for phenyl rings, tert-butyl groups and internal alkynes, bicyclo[1.1.1]pentane (BCP) can improve the drug-like qualities of bioactive molecules. Therefore, the incorporation of high-value functional groups to BCP scaffold becomes an efficient synthetic strategy to design new bioisosteres in drug development. Herein a radical-mediated bromoalkylation of[1.1.1]propellane was disclosed, leading to brominated BCP derivatives. Bromoalkyl heteroarylsulfones were employed as dual-function reagents in the radical transformation, in which two functionalities, alkylheteroarylsulfone and bromine atom, were concurrently introduced into[1.1.1]propellane. These reactions proceeded rapidly, and were generally completed within 2 h at room temperature. A variety of new alkylheteroarylsulfone-substituted BCP derivatives were furnished with high product diversity. This protocol features excellent atom-economy, simple operation, and gram-scale preparation.

Key words: radicals, difunctionalization, ring opening, [1.1.1]propellane, bicyclo[1.1.1]pentane (BCP)