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Issue 8, 2016
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Nickel-catalyzed C-3 direct arylation of pyridinium ions for the synthesis of 1-azafluorenes

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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.

Graphical abstract: Nickel-catalyzed C-3 direct arylation of pyridinium ions for the synthesis of 1-azafluorenes

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Publication details

The article was received on 01 Apr 2016, accepted on 19 May 2016 and first published on 19 May 2016


Article type: Edge Article
DOI: 10.1039/C6SC01457G
Citation: Chem. Sci., 2016,7, 5581-5586
  • Open access: Creative Commons BY-NC license
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    Nickel-catalyzed C-3 direct arylation of pyridinium ions for the synthesis of 1-azafluorenes

    J. Desrosiers, X. Wei, O. Gutierrez, J. Savoie, B. Qu, X. Zeng, H. Lee, N. Grinberg, N. Haddad, N. K. Yee, F. Roschangar, J. J. Song, M. C. Kozlowski and C. H. Senanayake, Chem. Sci., 2016, 7, 5581
    DOI: 10.1039/C6SC01457G

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