Ethers are important structural linkages found in many organic compounds and are routinely used as protecting groups. Traditional methods for the preparation of ethers R-O-R' such as the Williamson ether synthesis involve reaction of an alkyl halide R-X with an alcohol R'-OH.  We have developed a conceptually unique ether synthesis based on C-H functionalization that enables the oxidative coupling of sp3-hybridized C-H bonds in substrates R-H with alcohols R'-OH to give ethers R-O-R' in high yield.  The use of a copper catalyst system in conjunction with an inexpensive oxidant of minimal environmental impact allows for the C-H etherification of a range of alcohols with even strong, unactivated C-H bonds such as those in cyclohexane. Catalytic results demonstrating this novel transformation will be discussed alongside strategies to optimize this new C-H etherification protocol.

Copper catalyzed <i>sp</i><sup>3</sup>-C-H bond etherifcation

244th National Meeting (2012)

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Copper catalyzed sp3-C-H bond etherifcation

Copper catalyzed sp³-C-H bond etherifcation