Synfacts 2018; 14(05): 0537
DOI: 10.1055/s-0037-1609466
DOI: 10.1055/s-0037-1609466
Polymer-Supported Synthesis
Mechanochemical Generation of HCN from K3[Fe(CN)6]: A Novel Strecker Protocol
Bolm C.
Mocci R.
Schumacher C.
Turberg M.
Puccetti F.
Hernández JG.
* RWTH Aachen, Germany; Cittadella Universitaria, Monserrato and University of Firenze, Sesto Fiorentino, Italy
Mechanochemical Activation of Iron Cyano Complexes: A Prebiotic Impact Scenario for the Synthesis of α-Amino Acid Derivatives.
Angew. Chem. Int. Ed. 2018;
57: 2423-2426
Mechanochemical Activation of Iron Cyano Complexes: A Prebiotic Impact Scenario for the Synthesis of α-Amino Acid Derivatives.
Angew. Chem. Int. Ed. 2018;
57: 2423-2426
Further Information
Publication History
Publication Date:
17 April 2018 (online)
Key words
Strecker reaction - mechanochemical activation - carbonyls - amines - potassium ferricyanide - aminonitriles
Significance
A Strecker reaction of carbonyl compounds, primary amines, and potassium ferricyanide was carried out in the presence of SiO2 under ball-milling conditions to give the corresponding α-aminonitriles in 56–73% yield (eq. 1, 11 examples). The hydration of α-aminonitrile A also proceeded under ball-milling conditions to afford the corresponding amino amide in 51% yield (eq. 2).
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Comment
In situ generation of HCN was found to take place through mechanochemical activation of potassium ferricyanide {K3[Fe(CN)6]} by ball-milling in the presence of SiO2. The resulting HCN was trapped in situ by a Strecker reaction with benzaldehyde and benzylamine to give A.
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