Table 18
Hydrogenation of quinoline derivatives and other N-heterocycles mediated by IrO
2 NPs. Left
neighbouring substituents, right
none or remote
substituents
Z
R
1
R
2
Yield (%)
a
Z
R
1
R
2
Yield (%)
b
CH
H
2-Me
98
CH
H
H
98 (<5)
CH
H
3-Me
98
CH
H
2-Ph
97 (43)
CH
H
2-NH
2
96
CH
H
4-Me
42 (0)
CH
6-Me
2-Me
97
CH
H
6-Me
98 (<5)
CH
8-Me
H
98
CH
H
6-MeO
97 (<5)
CH
6-Br
2-Me
98
CH
6-NH
2
H
96 (0)
CH
8-Br
2-Me
97
CH
H
7-Me
97 (18)
N
H
2-Me
96
CH
8-Cl
H
95 (31)
N
H
2,3-dimethyl
97
N
H
H
98 (<5)
N
5-Me
H
91
N
H
2-Ph
96 (<5)
Reaction conditions: Substrate (0.2 mmol), IrO
2 NPs (1.2 mg, 0.04 mmol), MeOH (2 mL), 24 h. I
a
H
2 balloon, RT. Isolated yields
b
H
2 (60 bar), 60
C. Isolated yields (H
2 balloon and RT in brackets)
Iridium Nanoparticles for Hydrogenation Reactions
419