Photochemical reactions are an appealing strategy for chemical synthesis because they can proceed at room temperature under relatively gentle conditions, use light as a non-toxic reagent, and can be used to access unique products. Photoinduced electron transfer, triplet sensitization, photocleavage, and photocycloaddition reactions are just some examples of photochemical reaction pathways. Recently our research group introduced excited state proton transfer (ESPT) as an alternative means of facilitating organic transformations with light. In this presentation we will share our efforts using naphthol as an ESPT dye for the photocatalytic protonation of a silyl enol ether with phenol as the sacrificial proton source. We will then discuss our work to expand the utility of this reaction by using chiral ESPT dyes for the enantioselective protonation of an organic substrate. Finally, we will share our more recent progress in photodynamically resolving BINOL using an ESPT reaction.

Organic transformations via excited state proton transfer

255th National Meeting (2018)

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