1267003-62-2Relevant academic research and scientific papers
Potassium thiocyanate as source of cyanide for the oxidative α-cyanation of tertiary amines
Wagner, Alexander,Ofial, Armin R.
, p. 2848 - 2854 (2015)
Oxidation at the sulfur of the safe-to-handle potassium thiocyanate releases cyanide units that are trapped in the presence of co-oxidized tertiary amines to form α-amino nitriles. These cyanations work in aqueous solutions and do not require a catalyst,
A metal-free direct C (sp3)-H cyanation reaction with cyanobenziodoxolones
Sun, Ming-Xue,Wang, Yao-Feng,Xu, Bao-Hua,Ma, Xin-Qi,Zhang, Suo-Jiang
supporting information, p. 1971 - 1975 (2018/03/23)
A metal-free protocol of direct C(sp3)-H cyanation with cyanobenziodoxolones functioning as both cyanating reagents and oxidants was developed. Unactivated substrates, such as alkanes, ethers and tertiary amines, were thereby transformed to the corresponding nitriles in moderate to high yields. Mechanistic studies indicated that the cyanation proceeded with two potential pathways, which is highly dependent on the substrates: (1) a free radical case for alkanes and ethers and (2) an oxidative case for tertiary amines.
Method for synthesizing alpha-aminonitrile by adopting AIBN as individual cyan source
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Paragraph 0018-0020; 0022, (2017/09/01)
The invention relates to a method for synthesizing alpha-aminonitrile by adopting AIBN as an individual cyan source. The method comprises the following steps: adding tertiary amine into a container, sequentially adding 2,2'-azodiisobutyronitrile (AIBN), p
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.
