有机化学 ›› 2019, Vol. 39 ›› Issue (11): 3013-3025.DOI: 10.6023/cjoc201904044 上一篇    下一篇

所属专题: 有机光催化合辑

综述与进展

基于α-羰基重氮化合物参与的N-H插入反应的研究进展

封佳俊b, 易享炎b, 傅耀锋b, 于杨b, 黄菲ab*()   

  1. a南京师范大学食品与制药工程学院 南京 210023
    b 南京工业大学药学院 南京 211816
  • 收稿日期:2019-04-16 发布日期:2019-07-09
  • 通讯作者: 黄菲 E-mail:huangfei0208@yeah.net
  • 基金资助:
    国家自然科学基金(21901124);江苏省高等学校自然科学研究面上项目(19KJB150032);中国博士后科学基金(2019M651809);江苏省先进生物制造创新中心(XTE1850);安徽省博士后科研活动经费(2018B252)

Progress in N-H Insertion Reaction of α-Diazocarbonyl Compounds

Feng Jiajunb, Yi Xiangyanb, Fu Yaofengb, Yu Yangb, Huang Feiab*()   

  1. a School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023
    a School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816
  • Received:2019-04-16 Published:2019-07-09
  • Contact: Huang Fei E-mail:huangfei0208@yeah.net
  • Supported by:
    the National Natural Science Foundation of China(21901124);the Jiangsu University Natural Science Research Program(19KJB150032);the China Postdoctoral Science Foundation(2019M651809);the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture(XTE1850);the Anhui Province Postdoctoral Science Foundation(2018B252)

α-羰基重氮化合物易于制备,在光照和加热等条件下脱去氮气形成高反应活性的卡宾中间体,通过卡宾介导的各类反应可以高效构筑多种化学键,其中N-H插入反应可以实现高效构筑C-N键,在有机合成和药物合成领域得到广泛应用.总结了在过渡金属、有机小分子、生物大分子催化及光和热条件下实现α-羰基重氮化合物对N-H键的插入反应的研究进展,主要介绍了反应机理和合成应用,并对发展前景进行展望.

关键词: α-羰基重氮化合物, 卡宾, N-H插入反应, C-N键

The α-diazocarbonyl compounds are easy to prepare and can be dediazonized to highly reactive carbene intermediates under thermolytic or photolytic conditions. Chemical bonds can be efficiently constructed by carbene mediated reactions, including the insertion reaction of carbene into N-H bonds which is an effective method for constructing C-N bonds. The α-diazocarbonyl compounds have received extensive application in organic synthesis and pharmaceutical synthesis. The research progress in the insertion reaction of α-diazocarbonyl compounds into N-H bonds under transition metal, organic small molecules, biomacromolecule or photolytic and thermolytic conditions is summarized, including the reaction mechanism and synthesis applications. Finally, the prospects of this reaction are also discussed.

Key words: α-diazocarbonyl compound, carbene, N-H insertion reaction, C-N bond