Back to Search
Start Over
Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates
- 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.
- Subjects :
- Pyrrolidines
Vinyl Compounds
Potassium
chemistry.chemical_element
Stereoisomerism
Polyenes
Carbocation
010402 general chemistry
01 natural sciences
Biochemistry
Catalysis
Article
Styrenes
chemistry.chemical_compound
Radical clock
Borates
Molecule
Organic chemistry
Physical and Theoretical Chemistry
Molecular Structure
010405 organic chemistry
Aryl
Organic Chemistry
Combinatorial chemistry
0104 chemical sciences
chemistry
Reagent
Copper
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 18
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....b36c67d4aa0880f7d8fd1500ebc950de