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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: hisinlgls.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 (free Supporting Information)


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.

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proposed mechanism



Tandem Blaise-Alkenylation with Unactivated Alkynes: One-Pot Synthesis of α-Vinylated β-Enaminoesters from Nitriles

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