Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (12): 4340-4349.DOI: 10.6023/cjoc202207014 Previous Articles     Next Articles



许耀辉a, 吴镇a, 吴新鑫a, 朱晨a,b,*()   

  1. a 苏州大学材料与化学化工学部 江苏苏州 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:2022-07-06 修回日期:2022-08-14 发布日期:2022-09-01
  • 通讯作者: 朱晨
  • 作者简介:
  • 基金资助:
    国家自然科学基金(21971173); 国家自然科学基金(22171201)

Transition-Metal Free Radical-Mediated C—H Bond Alkynylation and Allylation of Ethers, Aldehydes and Amides

Yaohui Xua, Zhen Wua, Xinxin Wua, Chen Zhua,b()   

  1. a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
    b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2022-07-06 Revised:2022-08-14 Published:2022-09-01
  • Contact: Chen Zhu
  • About author:
    These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(21971173); National Natural Science Foundation of China(22171201)

Ethers, aldehydes, and amides are widely found in natural products and pharmaceutical molecules, and employed as inexpensive materials in synthetic chemistry. Radical-mediated heteroatomic α-C—H bond functionalization provides an efficient strategy for structural modification of ethers, aldehydes, and amides. New approaches of C—H alkynylation and allylation through phenyliodine bis(trifluoroacetate) (PIFA) induced hydrogen atom transfer (HAT) under visible-light irradiation are reported. The method is operationally simple, leading to the corresponding alkynylated and allylated products in moderate to good yields. The protocol features mild and transition-metal free conditions, broad functional group compatibility, and is adapted to a diversity of ethers, aldehydes, and amides as well as various alkynylating and allylating reagents.

Key words: radical reaction, alkynylation, allylation, transition-metal free, C—H bond functionalization