Synthesis of Vinylgermanes via the Au/TiO2-Catalyzed cis-1,2-Digermylation of Alkynes and the Regioselective Hydrogermylation of Allenes

Anastasia Louka; Manolis Stratakis

doi:10.1021/acs.orglett.1c00997

Synthesis of Vinylgermanes via the Au/TiO₂-Catalyzed cis-1,2-Digermylation of Alkynes and the Regioselective Hydrogermylation of Allenes

Org Lett. 2021 May 7;23(9):3599-3603. doi: 10.1021/acs.orglett.1c00997. Epub 2021 Apr 9.

Authors

Anastasia Louka¹, Manolis Stratakis¹

Affiliation

¹ Department of Chemistry, University of Crete, Voutes 71003, Heraklion, Greece.

PMID: 33835815
DOI: 10.1021/acs.orglett.1c00997

Abstract

In the presence of Au/TiO₂ (1 mol %), terminal alkynes react quantitatively with stoichiometric amounts of the unactivated digermane Me₃Ge-GeMe₃, forming exclusively cis-1,2-digermylated alkenes. We also establish the Au/TiO₂-catalyzed hydrogermylation of terminal allenes with Et₃GeH, which exhibits a highly regioselective mode of addition on the more substituted double bond forming vinylgermanes. Additionally, we provide preliminary results regarding the Pd nanoparticle-catalyzed C-C coupling of 1,2-digermyl alkenes with aryl iodides.