American Chemical Society
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Synthesis of 2‑Aryl- and 2‑Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β‑Aminoethyl Trifluoroborates

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journal contribution
posted on 2016-05-10, 02:48 authored by Chanchamnan Um, Sherry R. Chemler
2-Arylpyrrolidines occur frequently in bioactive compounds, and thus, methods to access them from readily available reagents are valuable. We report a copper-catalyzed intermolecular carboamination of vinylarenes with potassium N-carbamoyl-β-aminoethyltrifluoroborates. The reaction occurs with terminal, 1,2-disubstituted, and 1,1-disubstituted vinylarenes bearing a number of functional groups. 1,3-Dienes are also good substrates, and their reactions give 2-vinylpyrrolidines. Radical clock mechanistic experiments are consistent with the presence of carbon radical intermediates and do not support participation of carbocations.