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

Yamamoto, Takeshi; Ishibashi, Aoi; Koyanagi, Masashi; Ihara, Hideki; Eichenauer, Nils; Suginome, Michinori

doi:10.1246/bcsj.20170026

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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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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.

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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 - 24 Hours access

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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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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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