Synthesis of Secondary Amines via N-(Benzoyloxy)amines and Organoboranes

A variety of primary amines (R−NH2) 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...

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Bibliographic Details
Published in:Journal of organic chemistry 1999-02, Vol.64 (3), p.803-806
Main Authors: Phanstiel, Wang, Q. X, Powell, D. H, Ospina, M. P, Leeson, B. A
Format: Article
Language:English
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Summary:A variety of primary amines (R−NH2) 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo981613l