Photoredox-Catalyzed Site-Selective Intermolecular C(sp<sup>3</sup>)–H Alkylation of Tetrahydrofurfuryl Alcohol Derivatives
R. ABE, Kazunori Nagao, Tomohiro Seki, Dai Hata, Yusuke Sasaki, Hirohisa Ohmiya
Abstract
High Resolution Image Download MS PowerPoint Slide 4′-Selective alkylation of nucleosides has been recognized as one of the ideal and straightforward approaches to chemically modified nucleosides, but such a transformation has been scarce and less explored. In this Letter, we combine a visible-light-mediated photoredox catalysis and hydrogen atom transfer (HAT) auxiliary to achieve β-C(sp 3 )–H alkylation of alcohol on tetrahydrofurfuryl alcohol scaffolds and exploit it for 4′-selective alkylation of nucleosides. The reaction involves an intramolecular 1,5-HAT process and stereocontrolled Giese addition of the resultant radicals.
Topics & Concepts
AlkylationChemistryCatalysisIntramolecular forceAlcoholIntermolecular forceRadicalCombinatorial chemistryPhotoredox catalysisHydrogen atomMedicinal chemistryOrganic chemistryMoleculeAlkylPhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques