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Photoredox Generation of N-Centered Hydrazonyl Radicals Enables the Construction of Dihydropyrazole-Fused <i>gem</i>-Difluoroalkenes

Qi-Sheng Gao, Zhuo Niu, Yang Chen, Jing Sun, Weiying Han, Jingyun Wang, Miao Yu, Mingdong Zhou

2021Organic Letters47 citationsDOI

Abstract

An efficient visible-light-promoted N-radical-mediated tandem radical cyclization/defluorinated alkylation of β,γ-unsaturated hydrazones, and α-trifluoromethyl alkenes is described. This protocol provides a general and effective route to synthesize various dihydropyrazole-fused gem-difluoroalkenes at moderate to excellent yields under redox-neutral, metal-free, and mild conditions.

Topics & Concepts

ChemistryRadicalTrifluoromethylAlkylationTandemCombinatorial chemistryRedoxPhotoredox catalysisPhotochemistryOrganic chemistryPhotocatalysisCatalysisAlkylComposite materialMaterials scienceFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Photoredox Generation of N-Centered Hydrazonyl Radicals Enables the Construction of Dihydropyrazole-Fused <i>gem</i>-Difluoroalkenes | Litcius