940-27-2Relevant articles and documents
Aminofluorene-Mediated Biomimetic Domino Amination-Oxygenation of Aldehydes to Amides
Ghosh, Santanu,Jana, Chandan K.
supporting information, p. 5788 - 5791 (2016/11/29)
A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5′-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of 18O2, 18O-amide was formed with excellent (95%) isotopic purity.
Copper-catalyzed rearrangement of oximes into primary amides
Sharma, Sumeet K.,Bishopp, Simon D.,Liana Allen,Lawrence, Ruth,Bamford, Mark J.,Lapkin, Alexei A.,Plucinski, Pawel,Watson, Robert J.,Williams, Jonathan M.J.
supporting information; experimental part, p. 4252 - 4255 (2011/08/22)
The atom-efficient and cost-effective rearrangement of oximes into primary amides is catalyzed by simple copper salts. The use of homogeneous Cu(OAc) 2 (1-2 mol %) was found to be effective for this transformation at 80 °C. The reaction was successful with either conventional or microwave heating. CuO and CuO/ZnO on activated carbon provided a competent reuseable heterogeneous catalyst which could be used in a batch process or in flow. Copper salts are much cheaper than the precious metals previously used for this rearrangement, and the reaction conditions are milder than those reported.
