Ag-Catalyzed Cyanomethylation of Amines Using Nitromethane as a C1 Source

Takuya Takashima; Hamdiye Ece; Taiga Yurino; Takeshi Ohkuma

doi:10.1021/acs.orglett.3c02256

Ag-Catalyzed Cyanomethylation of Amines Using Nitromethane as a C₁ Source

Org Lett. 2023 Aug 18;25(32):6052-6056. doi: 10.1021/acs.orglett.3c02256. Epub 2023 Aug 10.

Authors

Takuya Takashima¹, Hamdiye Ece¹, Taiga Yurino², Takeshi Ohkuma²

Affiliations

¹ Graduate School of Chemical Sciences and engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
² Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.

PMID: 37560921
DOI: 10.1021/acs.orglett.3c02256

Abstract

A new methodology to afford α-amino nitriles through oxidative cyanomethylation of amines using nitromethane as the methylene source in the presence of Me₃SiCN without the addition of an external oxidant was developed. A catalytic amount of AgCN and a stoichiometric amount of LiBF₄ cooperatively promoted the transformation. A wide variety of the amines, including both aromatic compounds and aliphatic ones, which are labile under oxidative conditions, were applicable to the reaction.