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C-C Bond Formation via Copper-Catalyzed Conjugate Addition Reactions to Enones in Water at Room Temperature

Bruce H. Lipshutz*, Shenlin Huang, Wendy Wen Yi Leong, Guofu Zhong and Nicholas A. Isley

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States, Email: lipshutzchem.ucsb.edu

B. H. Lipshutz, S. Huang, W. W. Y. Leong, G. Zhong, N. A. Isley, J. Am. Chem. Soc., 2012, 134, 19985-19988.

DOI: 10.1021/ja309409e (free Supporting Information)


Abstract

Mixing an enone, zinc powder, TMEDA, and an alkyl halide in an aqueous micellar environement containing catalytic amounts of Cu(I) and Au(III) enables conjugate additions in water at room temperature via in situ generated organocopper reagents in good yields. In the presence of Ag(I), the amounts of alkyl halide, Zn, and AuCl3 can be reduced dramatically.

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Key Words

1,4-additions, Zinc, green chemistry, organocopper chemistry


ID: J48-Y2012-3820