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Programmable Synthesis of Multiply Arylated Cubanes through C-H Metalation and Arylation

Ryo Okude, Genki Mori, Akiko Yagi*, Kenichiro Itami*

“Programmable Synthesis of Multiply Arylated Cubanes through C–H Metalation and Arylation”
Chem. Sci. 2020, accepted. DOI:10.1039/D0SC01909G

キュバン(C8H8)は、立方体構造を有する炭化水素である。近年、その特異な構造を活かした医農薬開発や材料への応用が注目を集めている。一方でその直接官能基化は困難とされ、キュバン誘導体は種類に限りがあった。今回我々は、新たなキュバン誘導体であるマルチアリールキュバン類の合成に成功した。リチウム塩基およびアルキル亜鉛を用いた直接オルトメタル化、続くパラジウム触媒によるアリール化によって、モノ-、ジ-、トリ-、およびテトラアリールキュバンをそれぞれ位置選択的に合成した。マルチアリールキュバンの初のプログラム合成法であり、これら新規分子群の今後の応用が期待される。

Cubane (C8H8), a cubic alkane, has long attracted attention owing to its unique 3D structure. In order to utilize the cubane scaffold widely in science and technology, a powerful method for synthesizing diverse cubane derivatives is required. Herein, we report the synthesis of mono-, di-, tri-, and tetraarylated cubanes. Directed ortho-metalation with lithium base/alkyl zinc and subsequent palladium-catalyzed arylation enabled C–H metalation and arylation of cubane. This reaction allows the late-stage and regioselective installation of a wide range of aryl groups, realizing the first programmable synthesis of diverse multiply arylated cubanes.

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