Dramatic Rate Acceleration of the Baylis-Hillman Reaction in Homogeneous Medium in the Presence of Water
Juexiao Cai, Zhenghong Zhou, Guofeng Zhao and Chuchi Tang*
*State Key Laboratory of Elemento-Organic Chemistry, Institute of
Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic
of China, Email: c.c.tang
eyou.com
J. Cai, Z. Zhou, G. Zhao, C. Tang, Org. Lett., 2002, 4, 4723-4725.
DOI: 10.1021/ol027197f
Abstract
In homogeneous H2O/solvent, the reaction rate of the Baylis-Hillman reaction of aromatic aldehydes and acrylonitriles or acrylates was greatly accelerated. Me3N, DMAP, DABCO, and urotropine were found to be good catalysts.
| R | EWG | Solvent | t (h) |
Yield (%, isol.) |
| 4-O2NC6H4 | CO2Me | MeOH | 2 | 86 |
| 4-O2NC6H4 | CO2Me | THF | 2.5 | 99 |
| 4-O2NC6H4 | CO2Me | 1,4-dioxane | 2.5 | 97 |
| 4-O2NC6H4 | CO2Me | MeCN | 3 | 88 |
| 2-Furan | CO2Me | MeOH | 2.5 | 91 |
| 2-Furan | CO2Et | EtOH | 4 | 96 |
| 2-Furan | CO2Bu | BuOH | 24 | 94 |
| 4-O2NC6H4 | CN | MeOH | 0.5 | 85 |
| C6H5 | CN | MeOH | 6 | 92 |
| 4-ClC6H4 | CN | MeOH | 2.5 | 79 |
see article for more examples
Key Words
ID: J54-Y2002-190
