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Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.
Org Lett. 2016 05 20; 18(10):2515-8.OL

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.

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Authors+Show Affiliations

Um C
Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260, United States.
Chemler SR
Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260, United States.

MeSH

BoratesCatalysisCopperMolecular StructurePolyenesPyrrolidinesStereoisomerismStyrenesVinyl Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

27160334

Citation

Um, Chanchamnan, and Sherry R. Chemler. "Synthesis of 2-Aryl- and 2-Vinylpyrrolidines Via Copper-Catalyzed Coupling of Styrenes and Dienes With Potassium β-Aminoethyl Trifluoroborates." Organic Letters, vol. 18, no. 10, 2016, pp. 2515-8.
Um C, Chemler SR. Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates. Org Lett. 2016;18(10):2515-8.
Um, C., & Chemler, S. R. (2016). Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates. Organic Letters, 18(10), 2515-8. https://doi.org/10.1021/acs.orglett.6b01259
Um C, Chemler SR. Synthesis of 2-Aryl- and 2-Vinylpyrrolidines Via Copper-Catalyzed Coupling of Styrenes and Dienes With Potassium β-Aminoethyl Trifluoroborates. Org Lett. 2016 05 20;18(10):2515-8. PubMed PMID: 27160334.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates. AU - Um,Chanchamnan, AU - Chemler,Sherry R, Y1 - 2016/05/10/ PY - 2016/5/11/entrez PY - 2016/5/11/pubmed PY - 2018/6/22/medline SP - 2515 EP - 8 JF - Organic letters JO - Org Lett VL - 18 IS - 10 N2 - 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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/27160334/Synthesis_of_2_Aryl__and_2_Vinylpyrrolidines_via_Copper_Catalyzed_Coupling_of_Styrenes_and_Dienes_with_Potassium_β_Aminoethyl_Trifluoroborates_ DB - PRIME DP - Unbound Medicine ER -