Synthesis of N-tert.-butyl aromatic amines via heterogeneous acid catalysis

Abstract

Heterogeneous acid catalysts have been employed in the synthesis of N-tert.-butyl aromatic amines from isobutene and arylamines. This technique provides a highly selective route to N-tert.-butylanilines, compounds not readily available by conventional alkylating methods. The selectivity of N-alkylation is highest when heterogeneous acid catalysts of moderate Brønsted acidity are used at temperatures of 100–180°C. The selectivity between N and ring alkylation is also highly dependent upon the type and location of substituents on the aromatic ring.