posted on 2016-05-10, 02:48authored byChanchamnan 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.