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C-H Bond Activation and C-C Bond Formation in the Reaction of 2,5-dimethylthiophene With TpMe2Ir Compounds

C-H Bond Activation and C-C Bond Formation in the Reaction of 2,5-dimethylthiophene With TpMe2Ir Compounds

Margarita Paneque, Manuel L Poveda, Ernesto Carmona, Verónica Salazar

Dalton Trans. 2005 Apr 21;(8):1422-7.

PMID: 15824780

Abstract:

The bulky 2,5-dimethylthiophene (2,5-Me2T) reacts at 60 degrees 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 beta-carbon of the Ir-thienyl unit. Free, substituted thiophenes, derived from the original 2,5-Me2T, may be isolated in this way.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP638028	2,5-Dimethylthiophene		638-02-8	Price

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