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Durham University

Department of Chemistry

Publication details for Prof. Andrew Beeby

Davidson, Ross, Hsu, Yu-Ting, Batchelor, Thomas, Yufit, Dimitry & Beeby, Andrew (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.

Author(s) from Durham

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.