A simple method for the oxidn. of primaryamines to the corresponding ketones in the presence of both moisture and air is described. Treatment of an amine with benzoyl peroxide in the presence of Cs2CO3, followed by warming of the hydroxylamine product to 50-70° leads directly to the ketone. The method is shown to be effective for both benzylic and aliph. substrates. [on SciFinder(R)]
Synthesis of Secondary Amines via <i>N</i>-(Benzoyloxy)amines and Organoboranes
作者:O. Phanstiel、Q. X. Wang、D. H. Powell、M. P. Ospina、B. A. Leeson
DOI:10.1021/jo981613l
日期:1999.2.1
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