Chan-Evans-Lam Cu(II)-Catalyzed C–O Cross-Couplings: Broadening Synthetic Access to Functionalized Vinylic Ethers

We report a general and effective Cu(OAc)2-catalyzed C–O cross-coupling synthesis of di- and trisubstituted vinylic ethers, using a combination of N-isopropylimidazole ligand and dicumyl peroxide as stoichiometric oxidant. This method couples functionalized vinylic pinacolboronates with various 1° and 2° alcohols to provide single-step syntheses of novel and structurally complex vinylic ethers. The optimized conditions do not require excess alcohol reactant and substantially suppress competing side reactions.