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Metal‐Free Electrochemical Coupling of Vinyl Azides: Synthesis of Phenanthridines and β ‐Ketosulfones
Author(s) -
Li Guodong,
Kong Xianqiang,
Liang Qi,
Lin Long,
Yu Ke,
Xu Bo,
Chen Qianjin
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001059
Subject(s) - chemistry , sodium azide , electrochemistry , catalysis , combinatorial chemistry , substrate (aquarium) , azide , metal , oxidative coupling of methane , organic chemistry , electrode , oceanography , geology
We reported an efficient and environmentally benign electrochemical synthesis of phenanthridines by oxidative coupling of vinyl azides with sodium azide or benzenesulfonyl hydrazides, for the first time. The reaction conditions are mild, and no additional metal‐catalyst or exogenous oxidants are needed. The protocol has broad substrate scope and high functional group tolerance. Furthermore, this green electrochemical procedure can be readily extended to the synthesis of β ‐ketosulfones. Gram scale reactions further demonstrate the practicability.