Organic Chemistry Portal

Abstracts

Search:

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.tangeyou.com

J. Cai, Z. Zhou, G. Zhao, C. Tang, Org. Lett., 2002, 4, 4723-4725.

DOI: 10.1021/ol027197f (free Supporting Information)


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

Baylis-Hillman Reaction


ID: J54-Y2002-190