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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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Supplementary files

Article information


Submitted
01 Apr 2016
Accepted
19 May 2016
First published
19 May 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 5581-5586
Article type
Edge Article

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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