Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives

Abstract

C ₃-Symmetric tris-benzyl-O-substituted hexahydroxytriphenylene (HHTP) was prepared through selective ring opening with DIBAL-H in 48% yield (38% from HHTP in a two-step synthesis) avoiding the use of noxious, expensive and limited market availability reagents, with complete recovery of the undesired C_s co-product that is quantitatively recovered and converted back into HHTP. The C₃-symmetric triphenylene product was further functionalized through substitution, deprotection and Mannich condensation reactions affording a series of C₃-symmetric functionalized scaffolds in good yields for supramolecular applications.