135
A transition-metal-assisted oxidative C(sp3)-H/N-H cross-coupling reaction of
N-alkoxyamides with aliphatic hydrocarbons is developed (Scheme 4.55) [39]. In
this reaction, nitrogen radicals would generate from the oxidation of N-alkoxyamides.
And the role of Ni catalyst is to lower the reactivity of the generated nitrogen
Ar
OR
N
O
H
20 mol% Ni(acac) 2
2.0 equiv DTBP
+
120 °C
O
H
Ar
OR
N
O
O
OMe
N
O
O
85%
OMe
N
O
O
87%
MeO
OMe
N
O
O
75%
Br
OMe
N
O
58%
O
OMe
N
O
64%
O
MeO
OMe
N
O
84%
O
F 3 C
OMe
N
O
O
83%
OMe
N
O
O
O
48%
OMe
N
O
50%
Ar
OR
N
O
H
O t Bu
Ar
OR
N
O
O
H
O t Bu
O
[Ni]
Ar
OR
N
O
[Ni]
Ar
OR
N
O
O
Scheme 4.55 Oxidative C(sp3)-H/N-H cross-coupling
4 Oxidative Radical Couplings