%0 Journal Article
%@ 1523-7060
%A Solovyev, A
%A Lacôte, E
%A Curran, DP
%D 2011
%F pittir:16242
%J Organic Letters
%N 22
%P 6042 - 6045
%T Ring lithiation and functionalization of imidazol-2-ylidene-boranes
%U http://d-scholarship-dev.library.pitt.edu/16242/
%V 13
%X N,N′-Dialkyl and N,N′-diaryl imidazol-2-ylidene-boranes and trifluoroboranes are rapidly lithiated at C4 of the imidazole ring, and the resulting intermediates have been quenched with an assortment of electrophiles to provide ring-functionalized imidazol-2-ylidene-boranes. Further deprotonation and functionalization of C5 have been demonstrated. Deboronation of the products by treatment with triflic acid or iodine and then methanol opens a route to C4/C5 functionalized imidazolium salts and imidazol-2-ylidenes. © 2011 American Chemical Society.