Chem. J. Chinese Universities ›› 2014, Vol. 35 ›› Issue (11): 2335.doi: 10.7503/cjcu20140267
• Organic Chemistry • Previous Articles Next Articles
LIU Xiaojing, ZHOU Hongyong, LIU Bing, LI Xiaona, SONG Shasha, LI Yunqing, WANG Jiaxi*()
Received:
2014-03-25
Online:
2014-11-10
Published:
2014-10-17
Contact:
WANG Jiaxi
E-mail:wangjiaxi@hebut.edu.cn
Supported by:
CLC Number:
TrendMD:
LIU Xiaojing, ZHOU Hongyong, LIU Bing, LI Xiaona, SONG Shasha, LI Yunqing, WANG Jiaxi. Hydrogenation of Acetophenone Promoted by Ruthenium Complexes of Modified Glucosamine Derivatives†[J]. Chem. J. Chinese Universities, 2014, 35(11): 2335.
Entry | Ligand | T/K | Conversion(%) | Entry | Ligand | T/K | Conversion(%) |
---|---|---|---|---|---|---|---|
1 | GlcN | 363 | 15.6 | 4 | L3 | 363 | 57.8 |
2 | L1 | 363 | 57.4 | 5 | L4 | 363 | 49.5 |
3 | L2 | 363 | 40.0 |
Table 1 Hydrogenation of acetophenone promoted by complexes of L1—L4 and Ru precursors*
Entry | Ligand | T/K | Conversion(%) | Entry | Ligand | T/K | Conversion(%) |
---|---|---|---|---|---|---|---|
1 | GlcN | 363 | 15.6 | 4 | L3 | 363 | 57.8 |
2 | L1 | 363 | 57.4 | 5 | L4 | 363 | 49.5 |
3 | L2 | 363 | 40.0 |
Entry | T/K | n(S)/n(C) | Conversion(%) | TOF/h-1 |
---|---|---|---|---|
1 a | 318 | 1000 | 4.5 | 15 |
2 a | 333 | 1000 | 11.1 | 37 |
3 a | 348 | 1000 | 24.3 | 90 |
4 a | 363 | 1000 | 49.5 | 165 |
5 a | 368 | 1000 | 67.2 | 224 |
6 a | 373 | 1000 | 96.6 | 322 |
7 a | 383 | 1000 | 96.3 | 321 |
8 a | 393 | 1000 | 96.5 | 322 |
9 a | 413 | 1000 | 96.9 | 323 |
10 b | 393 | 5000 | 51.0 | 850 |
11 b | 413 | 5000 | 74.2 | 1232 |
Table 2 Effects of temperature on hydrogenation of acetophenone catalyzed by RuCl2(PPh3)3/L4
Entry | T/K | n(S)/n(C) | Conversion(%) | TOF/h-1 |
---|---|---|---|---|
1 a | 318 | 1000 | 4.5 | 15 |
2 a | 333 | 1000 | 11.1 | 37 |
3 a | 348 | 1000 | 24.3 | 90 |
4 a | 363 | 1000 | 49.5 | 165 |
5 a | 368 | 1000 | 67.2 | 224 |
6 a | 373 | 1000 | 96.6 | 322 |
7 a | 383 | 1000 | 96.3 | 321 |
8 a | 393 | 1000 | 96.5 | 322 |
9 a | 413 | 1000 | 96.9 | 323 |
10 b | 393 | 5000 | 51.0 | 850 |
11 b | 413 | 5000 | 74.2 | 1232 |
Entry | Base | Conversion(%) | Entry | Base | Conversion(%) |
---|---|---|---|---|---|
1 | NEt3 | 0.7 | 5 | KOH | 49.5 |
2 | NaOH | 16.2 | 6 | i-PrOK | 60.3 |
3 | K2CO3 | 19.5 | 7 | i-PrOK+t-BuOH | 46.0 |
4 | t-BuOK | 34.1 |
Table 3 Effects of bases on catalyst activity*
Entry | Base | Conversion(%) | Entry | Base | Conversion(%) |
---|---|---|---|---|---|
1 | NEt3 | 0.7 | 5 | KOH | 49.5 |
2 | NaOH | 16.2 | 6 | i-PrOK | 60.3 |
3 | K2CO3 | 19.5 | 7 | i-PrOK+t-BuOH | 46.0 |
4 | t-BuOK | 34.1 |
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