Germatranes and carbagermatranes: (hetero)aryl and alkyl coupling partners in Pd-catalyzed cross-coupling reactions

In the past few decades, palladium-catalyzed cross-coupling reactions have taken root in the construction of a complex synthetic community. The development of organometallics has been an important objective in this field. Our group has focused on exploiting new germanium-based reagents and the corresponding catalytic processes. In the past three years, we have established new methods for the synthesis of structure-modified (hetero)aryl germatranes and alkyl carbagermatranes. Particularly for alkyl carbagermatranes, the stability to be compatible with various derivatization reactions and the high activity for transmetallation (e.g. base/additive-free for primary alkyl carbagermatranes) distinguish them from many reported nucleophiles. In this article, we would introduce (1) the development process of organogermanium reagents in palladium-catalyzed cross-couplings; (2) the history of germatrane-type systems and the breakthrough we have made in the field; (3) the outlook for (carba)germatranes and alkyl-GeMe3.

Automated summary

Palladium-catalyzed cross-coupling reactions play a crucial role in the complex synthetic field. Our research group focuses on developing new germanium-based reagents and catalytic processes. Over the past three years, we have established new methods for the synthesis of novel compounds, with particular emphasis on the unique properties of alkyl carbagermatranes.