Synthesis of Triaryltriazasumanenes

Abstract

C3-symmetric chiral triaryltriazasumanenes were successfully prepared in good yields by Pd-catalyzed cross-coupling reactions of chiral tris(methylthio)triazasumanene with various arylboronic acids. These chiral triaryltriazasumanenes showed very stable bowl chirality without racemization at room temperature. Single-crystal X-ray crystallography of the p-(trifluoromethyl)phenyl derivative revealed the formation of unidirectional π–π stacking columns that were connected by F⋯F interactions unlike the non-columnar crystal packing of tris(methanesulfonyl)triazasumanene.