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Programmable synthesis of multiply arylated cubanes through C-H metalation and arylation.

ABSTRACT: 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 tetra-arylated 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.

SUBMITTER: Okude R

PROVIDER: S-EPMC8159448 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Programmable synthesis of multiply arylated cubanes through C-H metalation and arylation.

Okude Ryo R Mori Genki G Yagi Akiko A Itami Kenichiro K

Chemical science 20200424 29

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 tetra-arylated cubanes. Directed ortho-metalation with lithium base/alkyl zinc and subsequent palladium-catalyzed arylation enabled C-H metalation and arylation of cubane. ...[more]

PMID: 34094145

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