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Issue 28, 2016
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The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes

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Abstract

A versatile palladium-free route for the synthesis of 4-aryl-substituted phenylpyridines (ppy), starting from tert-butyl 4-oxopiperidine-1-carboxylate, is reported. Reaction with an aryllithium, followed by trifluoroacetic acid dehydration/deprotection and oxidation with 2-iodoylbenzoic acid and finally phenylation, gave 4 ligands (L1–4H): 2,4-diphenylpyridine, 4-(4-methoxyphenyl)-2-phenylpyridine, 2-phenyl-4-(o-tolyl)pyridine and 4-mesityl-2-phenylpyridine. These ligands were coordinated to iridium to give the corresponding Ir(L)2(A) complexes (Ir1–7), where A = ancillary ligand acetylacetate or 2-picolinate. This was used to demonstrate that, through a combination of ancillary ligand choice and torsional twisting between the 4-aryl substituents of the ppy ligands, it is possible to tune the phosphorescent emission of the complexes in the range 502–560 nm.

Graphical abstract: The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes

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Supplementary files

Article information


Submitted
15 Apr 2016
Accepted
10 Jun 2016
First published
27 Jun 2016

This article is Open Access

Dalton Trans., 2016,45, 11496-11507
Article type
Paper

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(III) complexes

R. Davidson, Y. Hsu, T. Batchelor, D. Yufit and A. Beeby, Dalton Trans., 2016, 45, 11496
DOI: 10.1039/C6DT01461E

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