Although methylation and other alkylation reactions are commonplace, current methods require hazardous, toxic, and/or unstable reagents. Two alternative strategies to alkylate nucleophiles will be described.   In the first strategy, electrophilic diorganocarbonates are used for O-methylation and N-ethoxylation. Mechanistic studies suggest that O-methylation with dimethyl carbonate proceeds by direct methyl transfer from the carbonate to the nucleophile, in analogy to other electrophilic alkylating agents. In the second strategy, a nucleophilic methylating reagent is used in place of typical electrophilic methyl sources. Specifically, a Chan-Lam-type Cu-catalyzed oxidative coupling of methylboronic acid with carboxylic acids and phenols was developed.

Methylation and ethoxylation strategies employing non-hazardous, stable reagents

256th National Meeting (2018)

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