Journal
CHEMICAL SCIENCE
Volume 11, Issue 29, Pages 7672-7675Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc01909g
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Funding
- ERATO program of the JST [JPMJER1302]
- CREST program of the JST [JPMJCR19R1]
- JSPS KAKENHI [19H05463, 19K15537]
- MEXT (WISE program)
- World Premier International Research Center Initiative (WPI), Japan
- Grants-in-Aid for Scientific Research [19H05463, 19K15537] Funding Source: KAKEN
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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. Directedortho-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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