Publication | Open Access
Copper‐Catalyzed Divergent Trifluoromethylation/Cyclization of Unactivated Alkenes
104
Citations
63
References
2016
Year
Semipinacol RearrangementEngineeringAlkene MetathesisNatural SciencesDiversity-oriented SynthesisDivergent Trifluoromethylation/cyclizationOrganic ChemistryKinetic Isotope EffectOrganometallic CatalysisCatalysisChemistryHalogenationBiomolecular EngineeringTrifluoromethylation Reactions
Abstract Most of the precedent copper‐catalyzed trifluoromethylation reactions of unactivated alkenes concern terminal alkenes, and these processes are terminated in elimination, or nucleophilic addition, or semipinacol rearrangement, or CH bond functionalization steps. In this study, we develop a trifluoromethylation method for both unactivated terminal and internal alkenes to enable divergent late‐stage radical cyclization and achieve high molecular complexity. These cyclizations are well consistent with Baldwin’s rule. Furthermore, a kinetic isotope effect (KIE) study and control reactions were conducted, and a plausible mechanism is proposed. magnified image
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