Oxygen alkylation within complicated molecules is needed within medicinal chemistry and natural product synthesis due to the highly selective nature of the human body. These ethers provide the required functional group for drug delivery and general stabilization of the molecule. Specifically for alcohol methylation, the typical reagents used to synthesize methyl ethers are toxic and extreme electrophiles. In 2008 a young scientist died from acute exposure to TMSD, which is a common reagent for these reactions. We have been able to avoid these reagents by creating new conditions using the Chan-Evans-Lam oxidative cross coupling mechanism which eliminates electrophiles from the entire process. By using a copper catalyst, we are able to complete nucleophilic methylation with methylboronic acid. We have continued previous work on phenol methylation, by exploring different boron reagents for methylboronic acid. While Chan-Evans-Lam is a well established reaction, there is no literature about using this mechanism for cyclopropylation for aliphatic alcohols. Cyclopropyl ethers within complicated molecules provide unique properties that are beneficial for drug development and stabilization. We have been able to establish new conditions for oxidative cross coupling by using cyclopropylboronic acid and a base to aid in deprotonation of the alcohol.

Cham-Evans-Lam oxidative O-alkylation

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