The development of photocatalysis during the past ten years has had a profound impact on the synthetic chemistry community, allowing for the facile preparation of complex compounds from rather simple (and oftentimes readily available) starting materials. We have chosen to adapt one such methodology, namely a photocatalytic [2+2] cycloaddition reaction, for the preparation of DNA-encoded libraries. Thereby, DNA-tagged styrene derivatives were reacted with structurally diverse cinnamates in the presence of an iridium-based photocatalyst to forge a densely functionalized cyclobutane scaffold. Importantly, this reaction proceeded under mild conditions and in DNA-compatible aqueous media. Upon thorough reaction optimization, this transformation was utilized for the assembly of a DNA-encoded library that is composed of structurally diverse compounds within largely desirable property space.

Enabling photocatalytic [2+2] cycloadditions for the synthesis of DNA-encoded libraries

ACS Spring Meeting 2021

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