Electrocatalytic Aziridination Of Alkenes Mediated By Halogenion

Aziridine derivatives are important synthons and intermediates in a series of important reactions, such as ring opening, rearrangement, reduction and elimination reactions; they are also efficient building blocks in synthesis of chiral amines, amino acids, and amino alcohols. Many natural compounds with anti-tumor activities contain aziridine structural units such as mitomycin, actinomycin, etc. Therefore, efficient synthesis of aziridine products have attracted attentions and interests of organic chemists.This study based on a green electrochemical synthetic aziridination of olefins as the research object. The main research results summarized as follows:(1) Electrocatalytic aziridination of alkenes mediated by n-Bu4NIAn efficient electrocatalytic method for the synthesis of aziridine has been established, in which the reaction was carried out under constant current, and only required a single undivided electrolytic cell and a catalytic amount of n-Bu4 NI as catalyst. Notably, the reaction could also be operated smoothly in the absence of electrolyte and featured with extensive substrate scope. Mechanism study showed that the process was likely to be a free radical mechanism.(2) Protecting-group-free electrochemical synthesis of aziridinesThe Protecting-group-free synthesis of aziridines has been a challenging topic in organic chemistry. In the effort to realize protecting-group-free synthesis of aziridines, bromation of olefin was realized accidentally. Without use of toxic and pollutive bromine. The method was suitable for bromation of styrene derivatives, α,β-unsaturated ketones, aliphatic chain and cyclic olefins with NH4 Br as bromine source under constant current electrolysis. Notably, the method is efficient for gram-scale bromation of alkenes.