|
---|
Entry
|
Catalyst (PMA mol%)
|
Time (min)
|
Temp. (°C)
|
Conv. (%)b
|
TOF (−h)
|
---|
1
|
0.03 mol%
|
30
|
50
|
79
|
5,267
|
PMA@FeCo/GC@MSS
|
2
|
0.05 mol%
|
5
|
50
|
81
|
19,440
|
PMA@FeCo/GC@MSS
|
3
|
0.05 mol%
|
10
|
50
|
94
|
11,280
|
PMA@FeCo/GC@MSS
|
4
|
0.05 mol%
|
20
|
50
|
97
|
5,820
|
PMA@FeCo/GC@MSS
|
5
|
0.05 mol%
|
30
|
50
|
100
|
4,000
|
PMA@FeCo/GC@MSS
|
6
|
0.1 mol%
|
30
|
25
|
93
|
1,860
|
PMA@FeCo/GC@MSS
|
7
|
0.1 mol%
|
30
|
50
|
100
|
2,000
|
PMA@FeCo/GC@MSS
|
8
|
0.05 mol% PMA
|
30
|
50
|
95
|
3,800
|
9
|
FeCo/GC@MSSc
|
30
|
50
|
0
|
-
|
10
|
SiO2c
|
30
|
50
|
0
|
-
|
11
|
Recovered from number 5
|
30
|
50
|
100
|
4,000
|
12
|
Recovered from number 11
|
30
|
50
|
100
|
4,000
|
13
|
Recovered from number 12
|
30
|
50
|
100
|
4,000
|
14
|
Recovered from number 13
|
30
|
50
|
100
|
4,000
|
- aReaction conditions: 1,3-diphenyl-2-propyn-1-ol (0.19 ml, 1.0 mmol), phenol (1.2 mmol), and acetonitrile (5.0 mL). bDetermined by 1H NMR spectroscopy. Yields are based on the amount of propargylic alcohol. CAmount of compound based on calculated content in 0.05 mol% PMA@FeCo/GC@MSS, respectively.