Cubane, the Platonic hydrocarbon par excellence, is not just an esoteric textbook example. After its first synthesis in 1964 by Eaton et al., its study was neglected for a long time and only few research groups explored its exciting chemistry, maybe due to the unique structure and prejudices of its stability. Even though highly strained, the cubic carbon skeleton shows a remarkable kinetic stability, which allows for its use in organic chemistry, e.g., as a rigid linker. Recently, Tsanaktsidis et al. showed the validation of cubane as a bioisostere to benzene in different pharmacologically important drugs. But despite of its potential use as a bioisotere in medicinal drug development or as a rigid alkane linker in material sciences, the chemistry of this promising hydrocarbon is still underdeveloped. To fully utilize the cubane scaffold, new synthetic tools must be developed to allow access to a large variety of tailored compounds for a variety of applications in molecular electronics, drug development and materials science. In this sense we rolled the dice again by applying transition-metal-catalyzed cross-coupling reactions to functionalize the cubane molecule. Even though direct cross-coupling reactions remain tricky, key elements for cross-couplings reactions (B, Si, P, S, Sn, Zn) were introduced onto the cubane core for the first time. Furthermore, detailed investigations of C-C bond formations with this particular strained tertiary hydrocarbon were realized The basic organic chemistry and functional group interconversion of cubane is the object of ongoing research to prepare cubanes for modern applications.

Development of new tools for the functionalization of cubane

253rd National Meeting (2017)

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