Photocatalytic [2 + 2] Cycloaddition in DNA-Encoded Chemistry
Dominik K. Kölmel, Anokha S. Ratnayake, Mark E. Flanagan, Mei‐Hsuan Tsai, Cong Duan, Chao Song
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.
Topics & Concepts
ChemistryPhotocatalysisCycloadditionDNAPhotochemistryCombinatorial chemistryOrganic chemistryCatalysisBiochemistryChemical Synthesis and AnalysisClick Chemistry and ApplicationsSynthesis and Catalytic Reactions