2,6-Bis(pyrazol-1-yl)pyridine (1-bpp) as a General Ligand for the Negishi Alkylation of Alkylpyridinium Salts

Kristen M Baker; Olivia P Bercher; J Cameron Twitty; Thomas Mortimer; Mary P Watson

doi:10.1021/acs.joc.3c00665

2,6-Bis(pyrazol-1-yl)pyridine (1-bpp) as a General Ligand for the Negishi Alkylation of Alkylpyridinium Salts

J Org Chem. 2023 Jun 27. doi: 10.1021/acs.joc.3c00665. Online ahead of print.

Authors

Kristen M Baker¹, Olivia P Bercher¹, J Cameron Twitty¹, Thomas Mortimer¹, Mary P Watson¹

Affiliation

¹ Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.

PMID: 37368977
DOI: 10.1021/acs.joc.3c00665

Abstract

A Ni/1-bpp catalyst was demonstrated to be effective in the Negishi alkylation with multiple classes of alkylpyridinium salts, including α-primary and α-secondary. These conditions are also effective for benzylic pyridinium salts, demonstrating the successful Negishi alkylation of benzylic pyridinium salts for the first time. Further, 14 derivatives of 1-bpp were prepared with a variety of steric and electronic properties to study how these changes impact the success of the Negishi alkylation.