Synfacts 2018; 14(05): 0537
DOI: 10.1055/s-0037-1609466
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Mechanochemical Generation of HCN from K3[Fe(CN)6]: A Novel Strecker Protocol

Yasuhiro Uozumi
Go Hamasaka
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
Further Information

Publication History

Publication Date:
17 April 2018 (online)



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).



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.