Nickel-Catalyzed C-3 Direct Arylation of Pyridinium Ions for the Synthesis of 1-Azafluorenes. Academic Article uri icon

abstract

  • The direct arylation of pyridine substrates using non-precious catalysts is underdeveloped but highly desirable due to its efficiency to access important motifs while being extremely cost-effective. The first nickel-catalyzed C-3 direct arylation of pyridine derivatives to provide a new approach to valuable 1-azafluorene pharmacophore frameworks was developed. This transformation is accomplished using air-stable nickel catalyst precursors combined with phenanthroline ligands and tolerates a variety of substituents. Computational studies suggest facile oxidative addition via the pyridinium form, deprotonation, and a subsequent carbo-nickelation cyclization. Nickel homolysis/recombination permits isomerization to the stereochemical array needed for the final elimination.

published proceedings

  • Chem Sci

altmetric score

  • 1

author list (cited authors)

  • Desrosiers, J., Wei, X., Gutierrez, O., Savoie, J., Qu, B. o., Zeng, X., ... Senanayake, C. H.

citation count

  • 17

complete list of authors

  • Desrosiers, Jean-Nicolas||Wei, Xudong||Gutierrez, Osvaldo||Savoie, Jolaine||Qu, Bo||Zeng, Xingzhong||Lee, Heewon||Grinberg, Nelu||Haddad, Nizar||Yee, Nathan K||Roschangar, Frank||Song, Jinhua J||Kozlowski, Marisa C||Senanayake, Chris H

publication date

  • August 2016