Novel enantiomerically pure cyclopentadienyl- and indenyl-functionalized N-heterocyclic carbene ligands have been prepared by reaction of a chiral imidazole tosylate derivative with the corresponding cyclopentadienyl and indenyl lithium salts. Coordination of the Cp-functionalized NHC ligand to iridium and rhodium allowed the preparation of enantiomerically pure chelating cyclopentadienyl-functionalized Ir(III) and Rh(III) metal complexes. In contrast, the indenyl-functionalized NHC coordinates to iridium in a monodentate fashion, giving an Ir(I)-NHC complex containing a dangling indene group. © 2011 American Chemical Society.
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