Synthesis of Secondary Amines via N-(Benzoyloxy)amines and Organoboranes.
A variety of primary amines (R-NH(2)) were converted to their corresponding N-(benzoyloxy)amines (i.e., R-NHOCOPh) under biphasic conditions in excellent yields (63-90%). The intermediate N-(benzoyloxy)amines were converted to their N-ethylamine derivatives upon reaction with triethylborane in THF in good yield (54-89%). These experiments demonstrated the similar chemistry of N-chloro- and N-(benzoyloxy)amines with organoboranes.
Phanstiel
O.
O
Center for Diagnostics and Drug Development, Department of Chemistry, University of Central Florida, Orlando, Florida 32816, and Department of Chemistry, University of Florida, Gainesville, Florida 32611.
Wang
Q. X.
QX
Powell
D. H.
DH
Ospina
M. P.
MP
Leeson
B. A.
BA