168
N
+
H
N
20 mol % eosin Y
0.3 mol % G-RuO 2
20 mol % eosin Y
0.3 mol % G-RuO 2
20 mol % eosin Y
0.3 mol % G-RuO 2
H 2 O, hv, (λ>450 nm)
H 2 O, hv, (λ>450 nm)
D 2 O, hv, (λ>450 nm)
r.t.
N
NH
+ H 2
42a
43a
44a, 94 %
1)
N
+
H
N
r.t.
N
NH
+ D 2
42a
43a
44a, 93 %
2)
N Ph
+
H
N
r.t.
N
NH
+ H 2
42a
43a
44a
3)
H H
N Ph
D D
+
42a-D
42a : 42a-D = 1:1
44a: 93 %
44a-D: 92 %
K H /K D = 1.7:1
Conv. of 42a: 94 %
Conv. of 42a-D: 55 %
Scheme 5.17 Deuterium experiments for the CCHE reaction between tetrahydroisoquinoline and
indole
Scheme 5.18 Proposed mechanism for the CCHE reaction between tetrahydroisoquinoline and
indole
W. Ai et al.