Photoredox-Catalyzed C-H Acetoxylation and its Application in Flow

Berwanger, Michael

Student Work

Photoredox-Catalyzed C-H Acetoxylation and its Application in Flow

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Medicinal chemists are constantly looking for new methods to transform C-H bonds into more useful functional groups late in their synthetic pathway. Photoredox directed C-H functionalization provides a synthetic option for selective access to benzylic C-H sites under mild conditions with minimal overoxidation. The literature precedent for C-H directed acetoxylation largely requires undesirable conditions and is only applicable on specific substrates. Photoredox directed C-H acetoxylation can perform this transformation using mild conditions on a variety of substrates by taking advantage of key bond and environmental differences. Through methodological improvements, acetoxylation yields were drastically improved, and its application was further proven through preliminary substrate scopes. After it was determined that product degradation occurred, a flow system was constructed, and byproduct generation was successfully mitigated.

This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

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