Metalloamination/Cyclization of Zinc(II) Amides Derived from N,N-Dimethylhydrazinoalkenes—Applications for the Direct C-SP2 Functionalization of Aryl and Vinyl Electrophiles

Abstract

Treatment of N,N-dimethylhydrazinoalkenes with diethylzinc followed by exposure of the resulting ethylzinc amides to high vacuum drives a Schlenck redistribution metalloamination/cyclization to generate the corresponding bis(organozinc) intermediates in excellent conversions. Direct treatment of these with appropriate aryl or vinyl electrophiles in the presence of catalytic PdCl2 (DPEphos) provides the corresponding arylated or alkenylated pyrrolidines and piperidines with high efficiency.