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Photocatalytic [2 + 2] Cycloaddition in DNA-Encoded Chemistry Release Time:2020-04-02

Abstract:

The on-DNA synthesis of highly substituted cyclobutanes was achieved through a photocatalytic [2 + 2] cycloaddition reaction in aqueous solution. Readily available DNA-tagged styrene derivatives were reacted with structurally diverse cinnamates in the presence of an iridium-based photocatalyst, Ir(ppy)2(dtbbpy)PF6, to forge two new C(sp3)–C(sp3) bonds. This transformation was demonstrated to have excellent functional group tolerance and allowed for the facile installation of a variety of heteroaromatic substituents on a densely functionalized cyclobutane scaffold.


Org. Lett. 2020, 22, 8, 2908–2913

https://doi.org/10.1021/acs.orglett.0c00574

Link:https://pubs.acs.org/doi/10.1021/acs.orglett.0c00574


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