Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite

Atsushi Kaga, Hirohito Hayashi, Hiroyuki Hakamata, Miku Oi, Masanobu Uchiyama, Ryo Takita, Shunsuke Chiba

Angewandte Chemie International Edition · 2017 · 88 citations · 42 references

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Abstract

A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.

References

42