Jump to main content
Jump to site search

Issue 8, 2016
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements