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Deoxygenation of aza-aromatics

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Sulfoxides and aza-aromatic N-oxides were deoxygenated using a system of indium and pivaloyl chloride at room temperature to give the corresponding sulfides and aza-aromatics in high yields.
E. S. Park, S. Hwan, Lee, J. H. Lee, H. J. Rhee, C. M. Yoon, Synthesis, 2005, 3499-3501.


A mild and efficient general method for the deoxygenation of organic N-oxides such as azoxybenzenes, N-arylnitrones, and N-heteroarene N-oxides uses the  environmentally friendly Lewis acids Zn(OTf)2 and Cu(OTf)2.
A. Saini, S. Kumar, J. S. Sandhu, Synlett, 2006, 395-398.