Rapid and Effective Synthesis of α-Acyloxy-α-alkynyltrimethylsilanes

Tuan Zhao (1) , Riccardo Piccardi (1) , Laurent Micouin (2)

1 LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques
2 SSMIP - Synthèse et structure de molécules d'interet pharmacologique

α-Alkynyl-α′-trimethylsilylhydrazones are readily oxidized into diazo compounds under simple experimental conditions. These stable diazo species can in turn react with a range of carboxylic acids via a protonation−nucleophilic substitution sequence, leading to valuable α-acyloxy-α-alkynyl-trimethylsilanes. This procedure avoids the delicate preparation and manipulation of α-hydroxypropargyltrimethylsilanes.

Domaines: Chimie organique

Tuan Zhao, Riccardo Piccardi, Laurent Micouin. Rapid and Effective Synthesis of α-Acyloxy-α-alkynyltrimethylsilanes. Organic Letters, 2018, 20 (16), pp.5015-5018. ⟨10.1021/acs.orglett.8b02165⟩. ⟨hal-02113392⟩