Cyclometalations on the imidazo[1,2-a][1,8]naphthyridine framework

Daw, Prosenjit ; Ghatak, Tapas ; Doucet, Henri ; Bera, Jitendra K. (2013) Cyclometalations on the imidazo[1,2-a][1,8]naphthyridine framework Organometallics, 32 (15). pp. 4306-4313. ISSN 0276-7333

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Cyclometalation on the substituted imidazo[1,2-a][1,8]naphthyridine platform involves either the C3-aryl or C4'-aryl ortho carbon and the imidazo nitrogen N3'. The higher donor strength of the imidazo nitrogen in comparison to that of the naphthyridine nitrogen aids regioselective orthometalation at the C3/C4'-aryl ring with Cp*IrIII (Cp* = η5-pentamethylcyclopentadienyl). A longer reaction time led to double cyclometalations at C3-aryl and imidazo C5'-H, creating six- and five-membered metallacycles on a single skeleton. Mixed-metal Ir/Sn compounds are accessed by insertion of SnCl2 into the Ir–Cl bond. Pd(OAc)2 afforded an acetate-bridged dinuclear ortho-metalated product involving the C3-aryl unit. Metalation at the imidazo carbon (C5') was achieved via an oxidative route in the reaction of the bromo derivative with the Pd(0) precursor Pd2(dba)3 (dba = dibenzylideneacetone). Regioselective C–H/Br activation on a rigid and planar imidazonaphthyridine platform is described in this work.

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Source:Copyright of this article belongs to American Chemical Society.
ID Code:99976
Deposited On:27 Nov 2016 13:28
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