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Intermolecular Alkene Difunctionalization via Gold‐Catalyzed Oxyarylation

Shuyao Zhang, Chenhuan Wang, Xiaohan Ye, Xiaodong Shi

2020Angewandte Chemie International Edition128 citationsDOIOpen Access PDF

Abstract

Abstract The gold‐catalyzed intermolecular oxyarylation of alkenes is reported. This work employed the oxidative addition of aryl iodides to Me−DalphosAu + for the formation of a Au III −Ar intermediate. The better binding ability of alkenes over O nucleophiles ensured the success of intermolecular oxyarylation, giving desired products with a broad substrate scope and high efficiency (>50 examples with up to 95 % yield). One‐pot converting of methoxy groups into other nucleophiles allowed achieving alkene difunctionalization with the construction of C−N, C−S, and C−C bonds under mild conditions.

Topics & Concepts

NucleophileIntermolecular forceAlkeneChemistryCatalysisArylYield (engineering)Substrate (aquarium)Combinatorial chemistryMedicinal chemistryOrganic chemistryMoleculeMaterials scienceAlkylGeologyOceanographyMetallurgyCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions
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