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Download fileSynthesis of 2‑Aryl- and 2‑Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β‑Aminoethyl Trifluoroborates
journal contribution
posted on 2016-05-10, 02:48 authored by Chanchamnan Um, Sherry R. Chemler2-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.