Conjugate addition of mixed diorganozinc compounds and functionalized organozinc cuprates to nitroolefins.
[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.
Rimkus
Audrius
A
University of Bielefeld, Faculty of Chemistry, P.O. Box 10 01 31, Germany.
Sewald
Norbert
N