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

Davidson, Ross; Hsu, Yu-Ting; Batchelor, Thomas; Yufit, Dimitry; Beeby, Andrew

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


Authors

Yu-Ting Hsu

Thomas Batchelor

Dimitry Yufit



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.

Citation

Davidson, R., Hsu, Y., Batchelor, T., Yufit, D., & Beeby, A. (2016). The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(III)complexes. Dalton Transactions, 45(28), 11496-11507. https://doi.org/10.1039/c6dt01461e

Journal Article Type Article
Acceptance Date Jun 10, 2016
Online Publication Date Jun 27, 2016
Publication Date Jul 28, 2016
Deposit Date Aug 12, 2016
Publicly Available Date Mar 28, 2024
Journal Dalton Transactions
Print ISSN 1477-9226
Electronic ISSN 1477-9234
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 45
Issue 28
Article Number 11496
Pages 11496-11507
DOI https://doi.org/10.1039/c6dt01461e

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