Mild alkane functionalisation leading to ethers: oxidative alkoxylation of cyclohexane with dibromobis(phosphine)palladium(II) - sodium alkoxide system
Abstract
Dibromobis(phosphine)palladium(ii) complexes, PdBr2 (L)2 [L = PPh3, P(p-Tol)3], react with cyclohexane and an alcoholic solution of sodium alkoxide, NaOR (R = Me, Et, Pri), at 30-60 °C affording the corresponding alkyl cyclohex-1-enyl ethers, ROC6H9, in 30-140% yield on palladium both under argon and under air; benzene is inert under the reaction conditions, sodium tert-butoxide does not enter the hydrocarbon alkoxylation.