On-DNA Cross-Dehydrogenative Coupling Reaction toward the Synthesis of Focused DNA-Encoded Tetrahydroisoquinoline Libraries
Xin Wen, Zhiqiang Duan, Jiaxiang Liu, Weiwei Lu, Xiaojie Lu
Abstract
To expand the chemical space of DNA-encoded library (DEL) technology, we have developed the DNA-compatible cross-dehydrogenative coupling reaction between tetrahydroisoquinolines (THIQs) and a series of nucleophiles such as nitromethane, terminal alkynes, and so on. Both photo- and metal-promoted conditions have been successfully established for this C-1 derivation of THIQs, as exemplified by the addition of nitromethane. All of these new DNA-compatible transformations have paved the way for the divergent oriented synthesis of THIQ-focused DELs.
Topics & Concepts
ChemistryNitromethaneDNANucleophileCombinatorial chemistryCoupling reactionCoupling (piping)TetrahydroisoquinolineStereochemistryNanotechnologyOrganic chemistryBiochemistryEngineeringCatalysisMaterials scienceMechanical engineeringChemical Synthesis and AnalysisCarbohydrate Chemistry and SynthesisSynthesis and Biological Activity