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Oxidative Heck Arylation for the Stereoselective Synthesis of Tetrasubstituted Olefins Using Nitroxides as Oxidants


  • This work was financially supported by the Chinese Scholarship Council (stipend to Z.H.). We thank Dr. Peter Nesvadba, BASF Basel, for a gift of nitroxide 8 and Benjamin Vonhören for conducting some experiments.


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One, two, and three! Nitroxides and dioxygen serve as oxidants in highly stereoselective oxidative Pd-catalyzed Heck arylations in which aryl boronic acids are used to synthesize triarylalkyl-substituted olefins. The reactions occur under very mild conditions at room temperature. As an example, the threefold sequential arylation of methyl acrylate is the crucial step in the stereoselective synthesis of Z-Tamoxifen.