103
NH
H
O
Me
R 1
10 mol% Pd (OAc) 2
12 equiv TBHP
80 °C, 24 h
+ H 3 C
R 2
NH
O
Me
R 1
R 2
O
NH
O
Me
O
92%
NH
O
Me
O
Me
81%
NH
O
Me
O
71%
OMe
NH
O
Me
O
88%
F
NH
O
Me
O
Cl
84%
NH
O
Me
O
85%
Ac
NH
O
Me
O
68%
Cl
Cl
NH
O
Me
O
Cl
Me
95%
NH
O
Me
O
82%
Cl
COOMe
excess
Scheme 4.8 Oxidative cross-coupling of acetanilide and toluene
CH 3
Pd
TBHP
CHO
TBHP
O
Scheme 4.9 Generation of acyl radicals in the reaction process
NH
H
O
Me
R
5 mol% Pd (OAc) 2
4 equiv TBHP
DMSO, 100 °C
+ H 3 C
NH
O
Me
R
O
2 equiv.
up to 93% yield
Scheme 4.10 Oxidative coupling of acetanilide and toluene
4 Oxidative Radical Couplings