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Updated: Sep 29, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Conjugate addition of mixed diorganozinc compounds and functionalized organozinc cuprates to nitroolefins
Audrius Rimkus1, Norbert Sewald
1University of Bielefeld, Faculty of Chemistry, P.O. Box 10 01 31, Germany.
Abstract:
[reaction: see text] The copper-catalyzed conjugate addition of symmetrical and mixed diorganozinc compounds as well as functionalized diorganozinc cuprates to nitroolefins leads to synthetically versatile nitro compounds in moderate to good yields. Mixed TMSM-organozinc compounds are suitable reagents for conjugate addition, since the TMSM group is not being transferred. Ipso substitution is observed in the absence of a catalytic amount of copper(I) salt. The nitroalkene moiety in 3-nitroacrylates proved to be the predominant Michael acceptor.
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