Citation: Feng Jiajun, Yi Xiangyan, Fu Yaofeng, Yu Yang, Huang Fei. Progress in N-H Insertion Reaction of α-Diazocarbonyl Compounds[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3013-3025. doi: 10.6023/cjoc201904044 shu

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

Feng Jiajun ^b ,
Yi Xiangyan ^b ,
Fu Yaofeng ^b ,
Yu Yang ^b ,
Huang Fei ^a,b,,

a.
School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023
b.
School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816

Corresponding author: Huang Fei, huangfei0208@yeah.net
Received Date: 16 April 2019
Revised Date: 23 May 2019
Available Online: 9 November 2019
Fund Project: the Jiangsu University Natural Science Research Program 19KJB150032the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture XTE1850the National Natural Science Foundation of China 21901124the China Postdoctoral Science Foundation 2019M651809Project supported by the National Natural Science Foundation of China (No. 21901124), the Jiangsu University Natural Science Research Program (No. 19KJB150032), the China Postdoctoral Science Foundation (No. 2019M651809), the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture (No. XTE1850) and the Anhui Province Postdoctoral Science Foundation (No. 2018B252)the Anhui Province Postdoctoral Science Foundation 2018B252

Figures(28)

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.
- α-diazocarbonyl compound,
- carbene,
- N-H insertion reaction,
- C-N bond
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