%A A Solovyev
%A E Lac?te
%A DP Curran
%J Organic Letters
%T Ring lithiation and functionalization of imidazol-2-ylidene-boranes
%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.
%N 22
%P 6042 - 6045
%V 13
%D 2011
%R 10.1021/ol202516c
%L pittir16242