Borylated Dibenzoborepin: Synthesis by Skeletal Rearrangement and Photochromism Based on Bora-Nazarov Cyclization

Authors

  • Dr. Azusa Iida,

    1. Research Center for Materials Science and Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University and CREST (Japan) Science and Technology Agency (JST), Furo, Chikusa, Nagoya 464-8602 (Japan)
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  • Dr. Shohei Saito,

    1. Research Center for Materials Science and Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University and CREST (Japan) Science and Technology Agency (JST), Furo, Chikusa, Nagoya 464-8602 (Japan)
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  • Prof. Dr. Takahiro Sasamori,

    1. Institute for Chemical Research, Kyoto University, Gakasho, Uji, Kyoto 611-0011 (Japan)
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  • Prof. Dr. Shigehiro Yamaguchi

    Corresponding author
    1. Research Center for Materials Science and Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University and CREST (Japan) Science and Technology Agency (JST), Furo, Chikusa, Nagoya 464-8602 (Japan)
    • Research Center for Materials Science and Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University and CREST (Japan) Science and Technology Agency (JST), Furo, Chikusa, Nagoya 464-8602 (Japan)===

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  • This work was partly supported by CREST, JST, and a Grant-in-Aid for Scientific Research on Innovative Areas (Stimuli-responsive Chemical Species, No. 24109007) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. A. I. expresses her gratitude to the JSPS research fellowship for young scientists.

Abstract

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It's a boron kind of magic: A complex reaction sequence involving a skeletal rearrangement leads to 10-dimesitylboryl-substituted dibenzoborepin in a one-pot transformation in good yield. The borylborepin shows remarkable photochromic properties and undergoes a bora-Nazarov cyclization to give a deep-blue compound with an allyl cation-like C[BOND]B[BOND]C substructure.

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