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Δ
•
t-BuO
+
•
t-BuO OH
OH
t-BuO
OH
•
t-BuOO
H
•
OH
O
H
H
Ph
OH
H
N
N
•
Ph
CO2Et
Ph
CO2Et
HN
CO2Et
CO2Et
EtO2C
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A
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B
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– t-BuOH
O
O
H
H
O O
N
Ph
H
Ph
EtO2C
N
H
CO2Et
+
CO2Et
[O]
CO2Et
3
2f
C
O
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H
O
CO2Et
4
Scheme 3 Possible mechanism for the oxidative C=C bond cleavage of
1f with TBHP
In summary, we have developed an efficient oxidative
C=C bond cleavage of electron-deficient enamines promot-
ed by TBHP as oxidant to give the corresponding alkyl N-
aryloxamates or N-aryl amides. High yields of the products,
short reaction times, and moderate temperatures, as well as
neutral and metal-free conditions, are the salient features
of this method.
Acknowledgements
This research was supported by the Research Council of the University
of Tehran.
Supporting Information
Supporting information for this article is available online at
S
u
p
p
ortioInfgrmoaitn
S
u
p
p
ortiInfogrmoaitn
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–E