Pd-Catalyzed Alkynylation of 2‑Chloroacetates and 2‑Chloroacetamides with Potassium Alkynyltrifluoroborates

The synthesis of β,γ-alkynyl esters and amides using air-stable potassium alkynyltrifluoroborates as nucleophilic partners in a mild Suzuki–Miyaura cross-coupling reaction has been achieved. Propargyl esters and amides were obtained in high yields using a low catalyst loading, and the substrate scope of the reaction has been significantly improved over previous methods

Pd-Catalyzed Cross-Coupling of Potassium Alkenyltrifluoroborates with 2‑Chloroacetates and 2‑Chloroacetamides

A protocol for the stereocontrolled synthesis of (<i>E</i>)- and (<i>Z</i>)-β,γ-unsaturated esters and amides is reported. 2-Chloroacetates as well as secondary and tertiary 2-chloroacetamides were successfully employed as electrophiles in the Suzuki–Miyaura cross-coupling reaction with potassium (<i>E</i>)- and (<i>Z</i>)-alkenyltrifluoroborates, affording the corresponding products in high yield