Organic Letters · 2014 · 43 citations · 39 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCatalytic MechanismsCross-coupling ReactionsHeterocycle SynthesisOrganic SynthesisRadical ReactionsIron CouplingIron-catalyzed Cross-couplingIron-catalyzed OxidationMechanistic Studies Of Cross-couplingMild Reaction ConditionsOxidative CouplingOxidative Coupling ReactionsOxidative Cross-coupling
An alternative method to an iron-catalyzed radical oxidative cross-coupling reaction followed by 2-chloro-1,3-dithiane and aryl olefins for the synthesis of β-chloro substituent 1,3-dithiane products is presented. The described method has the advantage of mildness of the reaction conditions and tolerates a variety of functional groups. Preliminary mechanistic studies have confirmed the first example of a coupling of 1,3-dithiane with unactivated alkenes that proceeds via an iron-catalyzed oxidative radical intermediate along the reaction pathway.
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