138825-96-4Relevant articles and documents
Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes
Wippert, Nicolai A.,Jung, Nicole,Br?se, Stefan
supporting information, p. 568 - 572 (2019/09/03)
A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.
A General and Direct Reductive Amination of Aldehydes and Ketones with Electron-Deficient Anilines
Pletz, Jakob,Berg, Bernhard,Breinbauer, Rolf
, p. 1301 - 1317 (2016/05/02)
In our ongoing efforts in preparing tool compounds for investigating and controlling the biosynthesis of phenazines, we recognized the limitations of existing protocols for C-N bond formation of electron-deficient anilines when using reductive amination. After extensive optimization, we have established three robust and scalable protocols for the reductive amination of ketones with electron-deficient anilines, by using either BH3·THF/AcOH/CH2Cl2 (method A), with reaction times of several hours, or the more powerful combinations BH3·THF/TMSCl/DMF (method B) and NaBH4/TMSCl/DMF (method C), which give full conversions for most substrates within 10 to 25 minutes. The scope and limitations of these reactions have been defined for 12 anilines and 14 ketones.
Oxidative Bromination of Aromatic Amides using Sodium Perborate as Oxidant
Hanson, James R.,Harpel, Simone,Medina, Inmaculada C. Rodriguez,Rose, Dorian
, p. 432 - 433 (2007/10/03)
Sodium perborate in glacial acetic acid-acetic anhydride with potassium bromide and sodium tungstate as a catalyst, provides a novel system for the bromination of aromatic amides.
