Hetero(element)carboxylation of unsaturated organic substrates is useful due to the installation of a carboxylic acid as well as a synthetically versatile hetero(element)-functional group. We recently reported the first method to achieve boralative-carboxylation of vinyl arenes. The mild method uses redox-neutral copper catalysis and a single atmosphere of CO2 to obtain new boron functionalized α-aryl carboxylic acids, including non-steroidal anti-inflammatory drugs (NSAIDs) such as bora-ibuprofen, bora-indoprofen, bora flurbiprofen, and bora-naproxen. However, boracarboxylation of internal alkenes presents a challenge, due to both sterics and the possibility of side reactions such as isomerization and beta hydride elimination. Recent progress toward expanding the substrate scope through utilization of increased CO2 pressure will be presented.

Impact of increased CO2 pressure on substrate scope and boracarboxylation reaction efficiency

2019 Spring National Meeting

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