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Updated: Jan 15, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
A Simplified, One-Pot, Procedure for the Deoxygenative Alkylation of Aryl Bromides
Shane Plunkett1, Justin B Diccianni2, James Mulhearn2
1Discovery Process Research, Johnson & Johnson R&D, Spring House, Pennsylvania 19477, United States.
None:
Advancements in the field of C(sp2)-C(sp3) cross-coupling using alcohols as feedstocks have resulted in widespread adoption in analogue synthesis. Using high-throughput experimentation, an in situ alcohol activation with N-heterocyclic carbenes in DMA was discovered. Validation of the optimized, workup-free conditions suggested equivalent or greater reactivity to conditions where the alcohol is activated separately. The methodology was tested with a set of polar alcohols with drug-like properties, resulting in isolated product in 45/48 reactions.
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