Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 384-390.DOI: 10.6023/cjoc201909041 Previous Articles     Next Articles


李庆雪, 李梦伟, 时绍青, 季晓霜, 何春兰, 姜波, 郝文娟   

  1. 江苏师范大学化学与材料科学学院 徐州 221116
  • 收稿日期:2019-09-30 修回日期:2019-10-15 发布日期:2019-11-01
  • 通讯作者: 姜波, 郝文娟;
  • 基金资助:

PhI(OAc)2-Mediated Dediazodioxygenation of α-Diazo Carbonyls

Li Qingxue, Li Mengwei, Shi Shaoqing, Ji Xiaoshuang, He Chunlan, Jiang Bo, Hao Wenjuan   

  1. School of Chemistry&Materials Science, Jiangsu Normal University, Xuzhou 221116
  • Received:2019-09-30 Revised:2019-10-15 Published:2019-11-01
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21602087), the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions and the National College Student's Innovation and Entrepreneurship Training Program (Nos. 201810320156X, 201810320019Z).

A new PhI(OAc)2-mediated dediazodioxygenation of α-diazo carbonyls was reported. By using the characteristics of the in-situ-generated O-centered radicals from the interaction of PhI(OAc)2 and N-hydroxy phthalimide (or N-hydroxy succinimide), O-centered radical-triggered dioxygenation of α-diazo carbonyls was achieved in this transformation, which led to the synthesis of a series of α,α-dioxoarylketones and α,α-dioxoesters with moderate to good yields. Based on the experimental results and literature reports, the possible reaction mechanism was proposed, which involved O-centered radical addition, C-N bond homolysis and radical cross coupling. In addition, the reaction featured mild conditions and simple operation without any catalyst.

Key words: dioxygenation, dediazotization, α,α-dioxoarylketones, α,α-dioxoesters