Organic Letters · 2022 · 27 citations · 44 references
Natural SciencesChemistryCatalysisOrganic ChemistryReaction EngineeringCatalytic MechanismsCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisArene FunctionalizationCatalytic Reaction MechanismsFuran FormationMild Reaction ConditionsRegioselectivityRing-forming ReactionsSubstrate ScopeSubstrate Scope Expansion
Herein, we report carbene-mediated benzannulation of vinyl sulfoxonium ylides with electron-deficient alkynes and alkenes to synthesize oxygenated arenes. This protocol features excellent regioselectivity, a broad substrate scope, and mild reaction conditions. Mechanistic studies revealed that the reaction proceeds through furan generation, cycloaddition, ring cleavage, and aromatization cascades. The synthesized arenes have been utilized in diverse product transformations and arene ring homologation.
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Jakub Durka, Joanna Turkowska, Dorota Gryko · ACS Sustainable Chemistry & Engineering · 2021 · 241 citations · Full text
Frank M. Hauser, Richard P. Rhee · The Journal of Organic Chemistry · 1978 · 181 citations
Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis
Janakiram Vaitla, Annette Bayer · Synthesis · 2018 · 119 citations · Full text
An annelation route to quionones
George A. Kraus, H. Sugimoto · Tetrahedron Letters · 1978 · 119 citations