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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

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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… Click to show full abstract

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.

Keywords: iodo naphthylboronic; oligo naphthalene; activation based; naphthalene diyl

Journal Title: Bulletin of the Chemical Society of Japan
Year Published: 2017

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