Determination of the π-Accepting Properties of Borate-, Aluminate-, and Gallate-Functionalized N-Heterocyclic Carbenes by 77Se NMR Spectroscopy.

ABSTRACT

Anionic N-heterocyclic carbenes with weakly coordinating borate, aluminate, and gallate moieties of the type [(F5C6)3E-NHC]- (E = B, Al, Ga) were isolated as lithium salts by the lithiation of 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene (IMes) or 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (IDipp) followed by the addition of E(C6F5)3 (E = B, Al, Ga). Treatment with elemental selenium afforded the lithium salts of the corresponding anionic selenourea derivatives [{(F5C6)3E-NHC}Se]- (NHC = IMes, E = B; NHC = IDipp, E = B, Al, Ga), which were examined, among other things, by means of 77Se{1H} NMR spectroscopy to assess the π-accepting properties of the WCA-NHC ligands in comparison with their neutral NHC congeners.