Mild alkane fimctionalisation leading to ethers: Oxidative alkoxylation of cyclohexane with the 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.