Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates

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Abstract

We have previously reported that the palladium-catalyzed cross-coupling reaction of air-stable potassium alkenyltrifluoroborates with aryl halides and triflates proceeds readily with good yields. Recent progress in outlining the scope and limitations of such reactions is described herein. The palladium-catalyzed cross-coupling reaction of potassium alkenyltrifluoroborates with aryl and heteroaryl halides and triflates proceeds readily with moderate to excellent yields. The alkenyl cross-coupling reaction can generally be effected using 2 mol % of PdCl₂(dppf)·CH₂Cl₂ as catalyst in i-PrOH−H₂O in the presence of t-BuNH₂ as the base. A variety of functional groups are tolerated in both partners, and the process is stereospecific with regard to the alkenyltrifluoroborate starting material.

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