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Near-Infrared-Light-Induced Iron(I) Dimer-Enabled Radical Cascade Reactions of Fluoroalkyl Bromides for the Synthesis of Ring-Fused Quinazolinones

Xiao-Di Su, Qiang Liu, Jin‐Tang Cheng, Zhixiang Wang, Xiang‐Yu Chen

2024Organic Letters15 citationsDOI

Abstract

The use of an earth-abundant and inexpensive iron complex as a catalyst, coupled with near-infrared (NIR) light as the energy source, for radical reactions with alkyl halides has been far less developed. In this study, we report NIR light-mediated iron(I) dimer-catalyzed radical cascade reactions of fluoroalkyl bromides for the synthesis of ring-fused quinazolinones bearing a difluoromethyl group. In this process, the 3-bromo-1,10-phenanthroline ligand facilitates the reactivity of [CpFe(CO) 2 ] 2, thereby improving the efficiency of the reaction.

Topics & Concepts

ChemistryDimerHalideRing (chemistry)CatalysisAlkylPhotochemistryReactivity (psychology)CascadeCombinatorial chemistryLigand (biochemistry)Organic chemistryPathologyReceptorAlternative medicineChromatographyMedicineBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry
Near-Infrared-Light-Induced Iron(I) Dimer-Enabled Radical Cascade Reactions of Fluoroalkyl Bromides for the Synthesis of Ring-Fused Quinazolinones | Litcius