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Issue 8, 2005
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C–H Bond activation and C–C bond formation in the reaction of 2,5-dimethylthiophene with TpMe2Ir compounds

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Abstract

The bulky 2,5-dimethylthiophene (2,5-Me2T) reacts at 60 °C with TpMe2Ir(C2H4)2 to give a mixture of two TpMe2Ir(III) hydride products, 3 and 4, that contain in addition a thienyl (3) or a thienyl-derived ligand (4). For the generation of 3 only sp2 C–H activation is needed, but the formation of 4 requires also the activation of an sp3 C–H bond and the formation of a new C–C bond (between vinyl and thienyl fragments). In the presence of 2,5-Me2T, compound 4 reacts further to produce a complex thiophenic structure (5, characterized by X-ray methods) that derives formally from two molecules of 2,5-Me2T and a vinyl fragment. Compounds 3–5 can be readily protonated by [H(OEt2)2][BAr′4] (Ar′ = 3,5-C6H3(CF3)2), with initial generation of carbene ligands (in the case of 3 and 5) as a consequence of H+ attack at the β-carbon of the Ir–thienyl unit. Free, substituted thiophenes, derived from the original 2,5-Me2T, may be isolated in this way.

Graphical abstract: C–H Bond activation and C–C bond formation in the reaction of 2,5-dimethylthiophene with TpMe2Ir compounds

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Article information


Submitted
05 Jan 2005
Accepted
28 Feb 2005
First published
09 Mar 2005

Dalton Trans., 2005, 1422-1427
Article type
Paper

C–H Bond activation and C–C bond formation in the reaction of 2,5-dimethylthiophene with TpMe2Ir compounds

M. Paneque, M. L. Poveda, E. Carmona and V. Salazar, Dalton Trans., 2005, 1422
DOI: 10.1039/B419414D

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