119
+
K 2 S 2 O 8 (2 equiv)
Bu 4 N
+ HSO 3
- (20 mol%)
CF 3 COOH
rt, 18 h
OH
OMe
HO
1.0 equiv
1.5 equiv
OH
OMe
HO
61%
Proposed mechanism
OH
OMe
K 2 S 2 O 8
OH
OMe
CF 3 COOH
HO
OH
OMe
HO
- 2 H
+
+
K 2 S 2 O 8 (2 equiv)
Bu 4 N + HSO 3
- (20 mol%)
CF 3 COOH
rt, 18 h
OH
OMe
HO
OH
OMe
HO
64%
OH
OH
Scheme 4.33 Oxidative cross-coupling of different phenols
CHO
R 1
+
R
3
R
2
20 mol% CuCl 2
2.5 equiv TBHP
5 equiv
80 °C, N 2
R
1
R
3
R
2
O
O
63%
O
69%
MeO
O
73%
O
75%
F
O
30%
MeO
OAc
O
64%
Scheme 4.34 Oxidative coupling of alkenes with aldehydes
4 Oxidative Radical Couplings
+
K 2 S 2 O 8 (2 equiv)
Bu 4 N
+ HSO 3
- (20 mol%)
CF 3 COOH
rt, 18 h
OH
OMe
HO
1.0 equiv
1.5 equiv
OH
OMe
HO
61%
Proposed mechanism
OH
OMe
K 2 S 2 O 8
OH
OMe
CF 3 COOH
HO
OH
OMe
HO
- 2 H
+
+
K 2 S 2 O 8 (2 equiv)
Bu 4 N + HSO 3
- (20 mol%)
CF 3 COOH
rt, 18 h
OH
OMe
HO
OH
OMe
HO
64%
OH
OH
Scheme 4.33 Oxidative cross-coupling of different phenols
CHO
R 1
+
R
3
R
2
20 mol% CuCl 2
2.5 equiv TBHP
5 equiv
80 °C, N 2
R
1
R
3
R
2
O
O
63%
O
69%
MeO
O
73%
O
75%
F
O
30%
MeO
OAc
O
64%
Scheme 4.34 Oxidative coupling of alkenes with aldehydes
4 Oxidative Radical Couplings