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
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).
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.
