Diethylzinc-Mediated Metalloamination-Alkylation of N, N-Dimethylhydrazinoalkenes. Catalysis of C-Zn Alkylation Using Simple Cu(I) Salts.

Metalloamination-alkylation of representative N,N-dimethyl-hydrazinoalkenes has been shown to be effectively catalyzed by CuBr-SMe2, CuCN, and Cul. The current method obviates the use of stoichiometric CuCN(LiCl)2 as a promoter for the electrophilic functionalization event.

1,2-Disubstituted Alkenes as Migratory Insertion Participants in Zn(II)-Promoted Metalloamination/Cyclization of N,N-Dimethylhydrazinoalkenes.

Diethylzinc-mediated metalloamination/cyclization of unsaturated N,N-dimethylhydrazines has been extended to the use of 1,2-disubstituted alkenes as N-Zn migratory insertion acceptors. Representative 2-arylethenes and vinylcyclopropanes readily serve as reaction participants in metalloamination/cyclization-allylation cascades.