Multifunctional Building Blocks Compatible with Photoredox-Mediated Alkylation for DNA-Encoded Library Synthesis
Shorouk O. Badir, Jaehoon Sim, Katelyn Billings, Adam Csakai, Xuange Zhang, Weizhe Dong, Gary A. Molander
Abstract
DNA-encoded library (DEL) technology has emerged as a novel interrogation modality for ligand discovery in the pharmaceutical industry. Given the increasing demand for a higher proportion of C(sp3)-hybridized centers in DEL platforms, a photoredox-mediated cross-coupling and defluorinative alkylation process is introduced using commercially available alkyl bromides and structurally diverse α-silylamines. Notably, no protecting group strategies for amines are necessary for the incorporation of a variety of amino-acid-based organosilanes, providing crucial branching points for further derivatization.
Topics & Concepts
AlkylationChemistryDerivatizationCombinatorial chemistryAlkylDNABranching (polymer chemistry)Ligand (biochemistry)Organic chemistryBiochemistryCatalysisHigh-performance liquid chromatographyReceptorChemical Synthesis and AnalysisRadical Photochemical ReactionsSynthesis and Catalytic Reactions