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

Authors :
Sherry R. Chemler
Chanchamnan Um
Source :
Organic Letters. 18:2515-2518
Publication Year :
2016
Publisher :
American Chemical Society (ACS), 2016.

Abstract

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.

Details

ISSN :
15237052 and 15237060
Volume :
18
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi.dedup.....b36c67d4aa0880f7d8fd1500ebc950de