Journal of the American Chemical Society · 2016 · 123 citations · 40 references
Natural SciencesChemistryMedicinal ChemistryGreen ChemistryOrganic ChemistrySynthetic Medicinal ChemistryChemical BondingCross-coupling ReactionsLate-stage FunctionalizationRetrosynthetic AnalysisScaffold DiversificationAlkyne Coupling ReactionsArene FunctionalizationFunctional Group ToleranceHeterocycle FunctionalizationLate-stage Functionalization Via Cross-couplingMild Reaction ConditionsScaffold SynthesisStereoselective Cross-coupling
A metal-free CH-CH-type coupling of arenes and alkynes, mediated by a multifunctional sulfoxide directing group, exploits nonprefunctionalized coupling partners, proceeds under mild conditions, is operationally simple, and exhibits high functional group tolerance. The products of the CH-CH coupling are highly versatile, and the metal-free process can be used for the construction and late-stage modification of important molecular scaffolds.
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