Monoalkylation of Primary Amines and N-Sulfinylamides Using Raney-Nickel

Significance

An efficient monoalkylation method of primary amines using Raney-nickel (Ra-Ni) was developed. Thus, the monoalkylation of aniline (0.2 mmol) was carried out with ethanol in the presence of Ra-Ni to give N-ethylaniline (2a) in 83% yield. The Ra-Ni was recovered by simple filtration and reused four times without any loss of catalytic activity (average: 81% yield). The mono-alkylation of several primary amines was also examined under similar reaction conditions to give the corresponding monoalkylated amines 2b-e in 79-86% yield.