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Title: Benzothiazolin-2-ylidene Complexes of Iridium(I)
Authors: Huynh, H.V. 
Meier, N.
Pape, T.
Hahn, F.E.
Issue Date: 5-Jun-2006
Citation: Huynh, H.V., Meier, N., Pape, T., Hahn, F.E. (2006-06-05). Benzothiazolin-2-ylidene Complexes of Iridium(I). Organometallics 25 (12) : 3012-3018. ScholarBank@NUS Repository.
Abstract: The reaction of allyl bromide with benzothiazole under neat conditions furnished 3-(2-propenyl)-benzothiazolium bromide, (H-1)Br, in high yield. Attempts to synthesize the corresponding carbene dimer by deprotonation of (H-1)+ led to the isolation of the rearrangement product 2,3-di(2-propenyl)-2′,3′-dihydro-2,2′-bisbenzothiazole (2). The reaction of [Ir(μ-OMe)(cod)]2 with the salt (H-1)Br unexpectedly afforded [IrBr(cod)(benzothiazole)] (3) (cod = 1,5-cyclooctadiene), which contained an N-coordinated unsubstituted benzothiazole ligand. The formation of carbene complexes of IrI with the benzothiazolin-2- ylidene ligand could be achieved via precoordination of the allyl substituent of (H-1)+ to [Ir(cod)-(MeCN)2]BF4 and subsequent deprotonation at the C2 position of (H-1)+ by addition of base. The use of NaH as external base yielded the square planar IrI complex 4 with an N-propyl-substituted carbene ligand, while deprotonation with KO tBu gave the five-coordinated IrI complex [IrBr(cod)(η2-1)], 5. Displacement of the cod ligand in complex 4 by two CO ligands afforded the complex [IrBr(CO)2(NHC)] (NHC = 3-propylbenzothiazolin-2-ylidene), 6, which allowed an estimation of the σ-donor capabilities of benzothiazolin-2-ylidene ligands. Compounds 1-6 have been characterized spectroscopically, and the molecular structures of (H-1)Br and 2-5 were determined by X-ray diffraction. © 2006 American Chemical Society.
Source Title: Organometallics
ISSN: 02767333
DOI: 10.1021/om060006i
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