Angewandte Chemie International Edition · 2019 · 72 citations · 77 references
Natural SciencesChemistryCatalysisOrganometallic ChemistryReaction EngineeringCross-coupling ReactionsPhotocatalysisPhotochemical SynthesisPhotochemistryRadical ReactionsMild Reaction ConditionsPhotocatalytic SynthesisPhotochemical FunctionalizationPhotoredox CatalysisPhotoredox FunctionalizationTransition Metal-catalyzed SynthesisTransition-metal-catalyzed FunctionalizationVisible-light Photocatalysis
Abstract We report the development of photoredox‐catalyzed and copper‐promoted trifluoromethoxylation of arenediazonium tetrafluoroborates, with trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxylation reagent. This new method takes advantage of visible‐light photoredox catalysis to generate the aryl radical under mild conditions, combined with copper‐promoted selective trifluoromethoxylation. The reaction is scalable, tolerates a wide range of functional groups, and proceeds regioselectively under mild reaction conditions. Furthermore, mechanistic studies suggested that a Cs[Cu(OCF 3 ) 2 ] intermediate might be generated during the reaction.
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Visible‐Light Photoredox Catalysis
Jun Xuan, Wen‐Jing Xiao · Angewandte Chemie International Edition · 2012 · 2.2K citations
Recent applications of arene diazonium salts in organic synthesis
Fanyang Mo, Guangbin Dong, Yan Zhang et al. · Organic & Biomolecular Chemistry · 2013 · 476 citations