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An Efficient CuI-Promoted Synthesis of Tri- and Tetrasubstituted Alkenes Using Organozinc Species

Song Xue*, Lin He, Yong-Kang Liu, Kai-Zhen Han, Qing-Xiang Guo

*Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China, Email:

S. Xue, L. He, Y.-K. Liu, K.-Z. Han, Q.-X. Guo, Synthesis, 2006, 666-674.

DOI: 10.1055/s-2006-926299

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An efficient method for the synthesis of multifunctionalized alkenes has been developed. In the presence of 5 mol% CuI as catalyst, an organozinc species CF3COOZnR reacted with α,β-acetylenic ketones and aldehydes in one pot providing trisubstituted alkenes in high yields with high stereoselectivity. The reaction with β-substituted-α,β-acetylenic ketones gave tetrasubstituted alkenes in good yields with Z-isomers as the major products.

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Key Words

organozinc species, α,β-acetylenic ketones, aldehydes, multifunctionalized alkenes, Baylis-Hillman adducts, CuI, multicomponent reactions

ID: J66-Y2006-520