Synthesis of secondary amines via N-(benzoyloxy)amines and organoboranes

Authors
Phanstiel, O Wang, QX Powell, DH Ospina, MP Leeson, BA
Citation
O. Phanstiel et al., Synthesis of secondary amines via N-(benzoyloxy)amines and organoboranes, J ORG CHEM, 64(3), 1999, pp. 803-806
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
3
Year of publication
1999
Pages
803 - 806
Database
ISI
SICI code
0022-3263(19990205)64:3<803:SOSAVN>2.0.ZU;2-G
Abstract
A variety of primary amines (R-NH2) were converted to their corresponding N -(benzoyloxy)amines (i.e., R-NHOCOPh) under biphasic conditions in excellen t 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 o f N-chloro- and N-(benzoyloxy)amines with organoboranes.