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M. Camats et al.
N
O
R
1
+
N
N R
R
R
1
+
[CuA NP] (2 mol%)
100 ºC, 12 h
glycerol
4 examples
Isolated yields: 87-91%
O
OH
R
1
+
[CuA NP] (2 mol%)
100 ºC, 12 h
glycerol
+
DMAP
O
N R
R
R
1
R
1 = Ph, 4-CH 3 -C 6 H 4
O
N R
R
R
1
or
R
1 = C 5 H 11
2 examples
Isolated yields: 81%-88%
O
NH 2
R
1
O
[CuA NP] (2 mol%)
100 ºC, 12 h
glycerol
+
HN
N
R
1
secondary
amine
HN
O
HN
Bu
HN Me
amine:
R
1 = Ph, C 5 H 11
secondary
amine
5 examples
Isolated yields: 81-96%
HN
O
HN
Bu
HN Me
amine: HNEt 2
R
1 = Ph, 4-CH 3 -C 6 H 4
2 examples
Isolated yields: 79%-89%
a) Synthesis of indolizines
b) Synthesis of benzofurans
c) Synthesis of quinolines
Scheme 8.15 Synthesis of indolizines, benzofurans, and quinolines catalyzed by CuA nanoparticles in glycerol [33] (for CuA, see Fig. 8.8)
Moreover, Shah et al. have recently reported the A
3 -coupling reaction for the
synthesis of propargylamines and pyrrolo[1,2-a]quinolines using a heterogenized
Cu catalyst (CuNPs@ZnO–polythiophene) at low catalyst loadings (Scheme 8.16)
O
N
R
1
+
+
N
R
1
N
[CuNP@ZnO-polythiophene]
(0.0052 wt%)
EG, 100 ºC, 100W
MW, 30 min
HN
O
HN
HN
HN
R
1 = Ph, 4-CH 3 -C 6 H 4, 4-CH 3 O-C 6 H 4, C 3 H 5, 4-NO 2 -C 6 H 4, 4-Br-C 6 H 4
amine =
secondary
amine
9 examples
Isolated Yield: 90-99%
Scheme 8.16 CuNPs@ZnO-polythiophene catalyzed synthesis of pyrrolo[1,2-a]quinolines in EG
under microwave irradiation [114]