Mild alkane functionalisation leading to ethers: oxidative alkoxylation of cyclohexane with the dibromobis(phosphine)palladium(II)–sodium alkoxide system

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.