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

Ky Mickelsen; Sean Zabawa; Tom Livinghouse

doi:10.1055/s-0036-1588578

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

Synlett. 2018 Jan;29(2):181-184. doi: 10.1055/s-0036-1588578. Epub 2017 Oct 12.

Authors

Ky Mickelsen¹, Sean Zabawa¹, Tom Livinghouse¹

Affiliation

¹ Department of Chemistry and Biochemistry, 103 CBB, Montana State University, Bozeman, MT 59717, USA livinghouse@chemistry.montana.edu.

Abstract

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.

Keywords: Cu(I) catalysis; allylation; metalloamination–cyclization.

Grants and funding

R01 GM116949/GM/NIGMS NIH HHS/United States