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Palladium-catalyzed alpha-arylation of tetramic acids.
J Org Chem. 2009 Jul 17; 74(14):5032-40.JO

Abstract

A mild, racemization-free, palladium-catalyzed alpha-arylation of tetramic acids (2,4-pyrrolidinediones) has been developed. Various amino acid-derived tetramic acids were cleanly arylated by treatment with 2 mol % of Pd(OAc)(2), 4 mol % of a sterically demanding biaryl phosphine, 2.3 equiv of K(2)CO(3) or K(3)PO(4), and aryl chlorides, bromides, or triflates in THF. With conventional heating, conversions >95% could be attained after 1 h at 80 degrees C, whereas microwave-induced heating led to much shorter reaction times (5 min at 110 degrees C). The electron density of the aryl electrophile had no effect on their reactivity: both electron-rich and electron-poor aryl chlorides and bromides or triflates led to good yields. Ortho-substituted aryl halides and heteroaryl halides, however, did not undergo the title reaction.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Storgaard M
Technical University of Denmark, Department of Chemistry, 201 Kemitorvet, DK-2800 Kgs. Lyngby, Denmark.
Dörwald FZ
No affiliation info available
Peschke B
No affiliation info available
Tanner D
No affiliation info available

MeSH

CatalysisMagnetic Resonance SpectroscopyMolecular StructurePalladiumPyrrolidinones

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19472991

Citation

Storgaard, Morten, et al. "Palladium-catalyzed Alpha-arylation of Tetramic Acids." The Journal of Organic Chemistry, vol. 74, no. 14, 2009, pp. 5032-40.
Storgaard M, Dörwald FZ, Peschke B, et al. Palladium-catalyzed alpha-arylation of tetramic acids. J Org Chem. 2009;74(14):5032-40.
Storgaard, M., Dörwald, F. Z., Peschke, B., & Tanner, D. (2009). Palladium-catalyzed alpha-arylation of tetramic acids. The Journal of Organic Chemistry, 74(14), 5032-40. https://doi.org/10.1021/jo900799y
Storgaard M, et al. Palladium-catalyzed Alpha-arylation of Tetramic Acids. J Org Chem. 2009 Jul 17;74(14):5032-40. PubMed PMID: 19472991.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed alpha-arylation of tetramic acids. AU - Storgaard,Morten, AU - Dörwald,Florencio Zaragoza, AU - Peschke,Bernd, AU - Tanner,David, PY - 2009/5/29/entrez PY - 2009/5/29/pubmed PY - 2009/9/29/medline SP - 5032 EP - 40 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 14 N2 - A mild, racemization-free, palladium-catalyzed alpha-arylation of tetramic acids (2,4-pyrrolidinediones) has been developed. Various amino acid-derived tetramic acids were cleanly arylated by treatment with 2 mol % of Pd(OAc)(2), 4 mol % of a sterically demanding biaryl phosphine, 2.3 equiv of K(2)CO(3) or K(3)PO(4), and aryl chlorides, bromides, or triflates in THF. With conventional heating, conversions >95% could be attained after 1 h at 80 degrees C, whereas microwave-induced heating led to much shorter reaction times (5 min at 110 degrees C). The electron density of the aryl electrophile had no effect on their reactivity: both electron-rich and electron-poor aryl chlorides and bromides or triflates led to good yields. Ortho-substituted aryl halides and heteroaryl halides, however, did not undergo the title reaction. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19472991/Palladium_catalyzed_alpha_arylation_of_tetramic_acids_ L2 - https://doi.org/10.1021/jo900799y DB - PRIME DP - Unbound Medicine ER -