The synthesis of 1-methylcyclopropyl aryl ethers represents an unsolved problem in organic chemistry. Access to such compounds could enable studies aimed at elucidating the metabolism of aryl cyclopropyl ethers by CYP450s. In this presentation, we will report our results on the development of a method to prepare methylcyclopropyl aryl ethers C via the cyclopropanation of the corresponding methylvinyl aryl ethers B, themselves obtained by the vinylation of phenols A using potassium vinyltrifluoroborates R. Optimization of the vinylation reaction to afford the corresponding vinylethers B will be presented, followed by the substrate and trifluoroborate scope. Then, development of the cyclopropanation reaction will be shown.

First synthesis of 1-methylcyclopropyl aryl ether via cyclopropanation of the corresponding methylvinyl aryl ethers

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ACS Fall 2022

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