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Steric and electronic effects on acetate-assisted cyclometallation of 2-phenylpyridines at [MCl2Cp*]2 (M = Ir, Rh)

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Abstract

The reactions of substituted 2-phenylpyridines at [MCl2Cp*]2 dimers (M = Ir, Rh) in the presence of NaOAc form cyclometallated complexes Cp*M(Phpyr)Cl. H/D exchange experiments and substrate competition experiments show that kinetic selectivity favours electron donating substituents whilst substrates with electron withdrawing substituents are favoured thermodynamically. Experiments with Ir are mostly irreversible under the conditions used whilst those for Rh are more easily reversible. For meta-substituted phenylpyridines steric effects are important, larger substituents leading to formation of the para-substituted cyclometallated product.

Graphical abstract: Steric and electronic effects on acetate-assisted cyclometallation of 2-phenylpyridines at [MCl2Cp*]2 (M = Ir, Rh)

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Article information


Submitted
29 Nov 2019
Accepted
06 Feb 2020
First published
06 Feb 2020

Dalton Trans., 2020, Advance Article
Article type
Paper

Steric and electronic effects on acetate-assisted cyclometallation of 2-phenylpyridines at [MCl2Cp*]2 (M = Ir, Rh)

D. L. Davies, K. Singh and N. Tamosiunaite, Dalton Trans., 2020, Advance Article , DOI: 10.1039/C9DT04581C

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