1569293-72-6Relevant academic research and scientific papers
Synthesis of α-aminonitriles via a FeSO4-mediated oxidative cyanation of tertiary amines with benzoyl cyanide and molecular oxygen or TBHP
Zhang, Lianpeng,Gu, Xin,Lu, Ping,Wang, Yanguang
, p. 2359 - 2363 (2016/04/19)
An iron-mediated oxidative cyanation of tertiary amines with benzoyl cyanide and molecular oxygen or TBHP has been achieved. This reaction furnished α-cyanated tertiary amines under mild reaction conditions in good to excellent yields (up to 94%) with gre
Iron-catalyzed generation of α-amino nitriles from tertiary amines
Wagner, Alexander,Han, Wei,Mayer, Peter,Ofial, Armin R.
, p. 3058 - 3070 (2014/03/21)
The use of iron(II) chloride as catalyst, trimethylsilyl cyanide as source of cyanide ions, and tert-butyl hydroperoxide as oxidant enabled the conversion of aromatic, benzylic, and aliphatic tertiary amines into α-Amino nitriles under mild conditions. Chemoselective functionalization of N-CH3 to N-CH2CN was achieved in the presence of Nbenzyl and N-alkyl groups. N,N-Dialkylanilines, PhNR2, with R=Et, Bu, Bn furnished the alkyl-(aryl)aminoacetonitriles PhN(R)CH2CN as the main products accompanied by α-Amino nitriles generated by ordinary a-cyanation of the aniline PhNR2. Formation of PhN(R)CH2CN was rationalized by oxidative degradation of N,N-dialkylanilines to N-alkylanilines, their condensation with formaldehyde, generated by oxidation of the solvent methanol, and final trapping of the thus formed iminium ions by cyanide.
