The Decarboxylative Blaise Reaction
Jae Hoon Lee, Bo Seung Choi, Jay Hyok Chang, Hee Bong Lee, Joo-Yong Yoon, Jaeick Lee and Hyunik Shin*
*Chemical Development Division, LG Life Sciences, Ltd./R&D,
104-1, Moonji-dong, Yusong-gu, Daejeon 305-380, Korea, Email: hisin
lgls.com
J. H. Lee, B. S. Choi, J. H. Chang, H. B. Lee, J.-Y. Yoon, J. Lee, H. Shin, J. Org. Chem., 2007, 72, 10261-10263.
DOI: 10.1021/jo701743m
Abstract
Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hünig's base provided β-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer, devoid of lachrymatory reagent, and is possible with less zinc chloride.
see article for more examples
proposed mechanism
Y. S. Chun, Y. O. Ko, H. Shin, S.-g. Lee, Org. Lett., 2009, 11, 3414-3417.
Key Words
Blaise Reaction, β-enamino esters
ID: J42-Y2007-4190
