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

Journal of the American Chemical Society 2012
Dmitrijs Lubriks, Igors Sokolovs, Edgars Sūna

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.

Keywords
Regioselective fragmentation, Cu(I) catalyst,
DOI
10.1021/ja305574k
Hyperlink
http://pubs.acs.org/doi/abs/10.1021/ja305574k

Lubriks, D., Sokolovs, I., Sūna, E. Indirect C–H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical λ3-Iodanes. Journal of the American Chemical Society, 2012, Vol.134, Iss.37, pp.15436-15442. ISSN 0002-7863. Available from: doi:10.1021/ja305574k

Publication language
English (en)