171
+
10 mol % Ru(bpy) 3 (PF 6 ) 2
10 mol % Co(dmgH) 2 pyCl
CD 3 CN, blue LEDs
r.t.
+ H 2
45
46
47 (13 %)
HN
PMP
H
COOEt
H
O
OEt
O
O
COOEt
COOEt
HN H
PMP
H
(15 %)
+
10 mol % Ru(bpy) 3 (PF 6 ) 2
10 mol % Co(dmgH) 2 pyCl
CH 3 CN, blue LEDs
r.t.
+ D 2 /HD/H 2
45-D
46
47/47-D
K H /K D = 1.86
HN
PMP
D
COOEt
H
O
OEt
O
O
COOEt
COOEt
HN H/D
PMP
H
10 mol % Ru(bpy) 3 (PF 6 ) 2
10 mol % Co(dmgH) 2 pyCl
CH 3 CN, blue LEDs
r.t.
+ H 2
45
49'
HN
PMP
D
COOEt
H
(~50 %)
N
PMP
H
COOEt
HN
PMP
H
COOEt
49
PMP = p-methoxphenyl
Scheme 5.21 Mechanistic study of the CCHE reaction of secondary amines with β-keto esters
Scheme 5.22 The CCHE reaction of isochromans with β-keto esters
5 Fourth-Generation Oxidative Cross-Coupling Reactions