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Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ3-Iodanes

By Dmitrijs Lubriks, Igors Sokolovs and Edgars Sūna

Abstract

A C–H bond of electron-rich heterocycles is transformed into a C–N bond in a reaction sequence comprising the formation of heteroaryl(phenyl)iodonium azides and their in situ regioselective fragmentation to heteroaryl azides. A Cu(I) catalyst ensures complete regiocontrol in the fragmentation step and catalyzes the subsequent 1,3-dipolar cycloaddition of the formed azido heterocycles with acetylenes. The heteroaryl azides can also be conveniently reduced to heteroarylamines by aqueous ammonium sulfide. The overall C–H to C–N transformation is a mild and operationally simple one-pot sequential multistep process

Topics: Regioselective fragmentation, Cu(I) catalyst
Publisher: ACC Publications
OAI identifier: oai:ortus.rtu.lv:14116
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