C–H Activation-Based Transformation of Naphthalenes to 3-Iodo-2-naphthylboronic Acid Derivatives for Use in Iterative Coupling Synthesis of Helical Oligo(naphthalene-2,3-diyl)s

Oligo(naphthalene-2,3-diyl)s were synthesized by iterative cross-coupling of 1,8-diaminonaphthalene-modified 3-iodo-2-naphthylboronic acids prepared from naphthalenes via Ir-catalyzed C–H borylation, Ru-catalyzed ortho-C–H silylation directed by an anthranilamide-modified boronyl group, and subsequent iododesilylation. The introduction of a chiral diol to the retained terminal boronyl group allowed selective induction of P- or M-helical conformations.