Synergistic Gold-Silicon Catalysis: Unravelling Alkynyl Gold Reactivity and Application to the High-Performance C-Alkynylation of Glycals.

ABSTRACT: Within the synergistic gold-silicon catalysis concept, we have reported here the efficient and highly α-stereoselective Au-Si-catalyzed alkyne transfer from 1-trimethylsilylalkynes to glycals, at room temperature and at low loading (0.2-1 mol%). The synthesized and bench-stable (F₅Ph)₃PAuNTf₂ complex was found instrumental to achieve such C-alkynylation reaction, through the in situ generation of both trimethylsilyl triflimide and alkynylgold complex from 1-trimethylsilylalkynes. This coupling has been deployed routinely on a wide combination of glycal donors and as efficiently with either aryl or alkyl 1-trimethylsilylalkyne aglycons, functionalized or not. This method could also be applied to the synthesis of a pseudo-C-disaccharide. DFT mechanistic inves

SUBMITTER: Pascaretti M 

PROVIDER: S-EPMC12498081 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature