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Updated: Jun 23, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Utilization of potassium vinyltrifluoroborate in the development of a 1,2-dianion equivalent
Gary A Molander1, Deidre L Sandrock
1Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Abstract:
Previous studies of orthogonally reactive dibora species led to the discovery of a unique reactivity pattern associated with potassium vinyltrifluoroborate. Upon hydroboration, the vinyltrifluoroborate generates a 1,2-diboraethane, which is distinct from the 1,1-dibora intermediates generated when traditional alkenyldialkylboron species undergo hydroboration. The 1,2-dianion equivalent thus generated can be envisioned as a building block for the linkage of two different electrophiles via palladium-catalyzed Suzuki-Miyaura cross-couplings.
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