First nickel-catalyzed 1,4-conjugate additions to α,β-unsaturated systems using triorganoindium compounds.

Pérez, I.; Pérez Sestelo, J.; Maestro, M. A.; Mouriño, A.; Sarandeses, L. A.


J. Org. Chem. 1998, 63, 10074–10076 (DOI: 10.1021/jo981830m).

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A novel, efficient nickel-catalyzed 1,4-conjugate addition of triorganoindium compounds to ,-unsaturated systems is described. Best results were obtained using Ni(COD)2. The range of groups susceptible of addition was studied using aryl and primary and tertiary alkyl organoindium compounds prepared from commercially available organolithium compounds by transmetallation with InCl3. Addition to enones, esters and nitriles occurred in yields ranging from 50 to 89%.