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The γ-selective, palladium-catalyzed cross-coupling of sodium (Z)-2-butenyldiethylsilanolate with a variety of aromatic bromides is reported. The protocol provides high yields (73-94%) and site selectivity (γ/α, 25:1 → &gt; 99:1) in the coupling of electron-rich, electron-poor, sterically hindered, and heteroaromatic bromides. The use of a configurationally homogeneous (Z)-silanolate, nontransferable ethyl groups, and a sterically bulky trialkylphosphonium tetrafluoroborate salt (t-BuCy(2)PH(+)BF(4)(-)) prepared directly from the corresponding air-stable phosphine•borane adduct are critical to the success of the method.

organic letters

γ-Selective Cross-Coupling of Allylic Silanolate Salts with Aromatic Bromides Using Trialkylphosphonium Tetrafluoroborate Salts Prepared Directly from Phosphine•Borane Adducts