Reductive N-alkylation of amides, carbamates and ureas

Article abstract of DOI:10.1016/S0040-4039(99)00211-7

A one pot selective mono N-alkylation of primary amides, thioamides, carbamates and ureas has been developed using aromatic and aliphatic aldehydes as alkylating agents and trifluoroacetic acid / triethylsilane as reagents. Application to an efficient synthesis of a primary amine from the corresponding aldehyde via the carbamate intermediate is presented.