Efficient Conversion of Alcohols into Primary Amines

Significance

A simple method for conversion of primary and secondary alcohols into primary amines via a modified Mitsunobu reaction was reported. Thus, to a mixture of alcohols 1, bis-tert-butyliminodicarboxylate and polystyrene resin bound triphenylphosphine in dichloromethane was added di-tert-butylazodicarbonate (DBAD) at 0 °C, and the reaction mixture was stirred for 30 minutes. The resulting mixture was treated with trifluoroacetic acid to give the corresponding primary amines 2 in 55-91% yield (9 examples).