Reductive N-alkylation of amides, carbamates and ureas

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 rifluoroacetic acidtriethylsilane as reagents. Application to an efficient synthesis of a primary amine from the corresponding aldehyde via the carbamate intermediate is presented.