Enantioselective Preparation of a Chiral-at-Metal Cp*Ir(NHC) Complex and Its Application in the Catalytic Diboration of Olefins

The reaction of (S,S)-1,3-di(methylbenzyl)imidazolium chloride with [Cp*IrCl2]2 in the presence of NaOAc affords the diastereoselective formation of a Cp*Ir(NHC) complex with a chelating ligand coordinated through the carbene and the ortho-position of one of the phenyl groups. The crystal structure of this new enantiomerically pure compound is described. The complex has been used in the catalytic diboration of olefins, providing high efficiencies and chemoselectivities on the organodiboronate products.