Flavin Metallaphotoredox Catalysis: Synergistic Synthesis in Water
Maheshwerreddy Chilamari, Jacob R. Immel, Pei-Hsuan Chen, Bayan M. Alghafli, Steven Bloom
Abstract
Combining a transition metal with a photocatalyst can drive modern synthetic chemistry. For transformations performed in water, this concept has been largely unexplored. We report the successful merger of a biocompatible flavin photocatalyst with a palladium catalyst to build isotopically enriched peptidomimetics, to mediate conjugate addition and C–H functionalization reactions, and to assemble unprotected proteinogenic and nonproteinogenic peptides, in water. We detail the important role of the ligand and the palladium oxidation state for controlling product selectivity when constructing synthetic peptides.
Topics & Concepts
Flavin groupCatalysisChemistryPalladiumCombinatorial chemistryPeptidomimeticPhotocatalysisLigand (biochemistry)SelectivityConjugateOxidation stateSurface modificationOrganic chemistryPeptideEnzymeMathematical analysisMathematicsReceptorPhysical chemistryBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions