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Preparation of tetrasubstituted 3-phosphonopyrroles through hydroamination: scope and limitations

Wouter Debrouwer (UGent) , Thomas Heugebaert (UGent) and Christian Stevens (UGent)
(2014) JOURNAL OF ORGANIC CHEMISTRY. 79(10). p.4322-4331
Author
Organization
Abstract
Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines. These starting compounds were obtained in two steps from commercially available beta-ketophosphonates. The method tolerates a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substituents at the 4-position via lithiation or halogenation.
Keywords
INTRAMOLECULAR HYDROAMINATION, :HIGHLY SUBSTITUTED PYRROLES, FUNCTIONALIZED PYRROLES, 2-PROPYNYL-1_3-DICARBONYL COMPOUNDS, AMINATION/ANNULATION REACTIONS, INTERMOLECULAR HYDROAMINATION, OLIGOSUBSTITUTED PYRROLES, POLYSUBSTITUTED PYRROLES, CATALYZED HYDROAMINATION, TERMINAL ALKYNES

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Citation

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MLA
Debrouwer, Wouter, Thomas Heugebaert, and Christian Stevens. “Preparation of Tetrasubstituted 3-phosphonopyrroles Through Hydroamination: Scope and Limitations.” JOURNAL OF ORGANIC CHEMISTRY 79.10 (2014): 4322–4331. Print.
APA
Debrouwer, W., Heugebaert, T., & Stevens, C. (2014). Preparation of tetrasubstituted 3-phosphonopyrroles through hydroamination: scope and limitations. JOURNAL OF ORGANIC CHEMISTRY, 79(10), 4322–4331.
Chicago author-date
Debrouwer, Wouter, Thomas Heugebaert, and Christian Stevens. 2014. “Preparation of Tetrasubstituted 3-phosphonopyrroles Through Hydroamination: Scope and Limitations.” Journal of Organic Chemistry 79 (10): 4322–4331.
Chicago author-date (all authors)
Debrouwer, Wouter, Thomas Heugebaert, and Christian Stevens. 2014. “Preparation of Tetrasubstituted 3-phosphonopyrroles Through Hydroamination: Scope and Limitations.” Journal of Organic Chemistry 79 (10): 4322–4331.
Vancouver
1.
Debrouwer W, Heugebaert T, Stevens C. Preparation of tetrasubstituted 3-phosphonopyrroles through hydroamination: scope and limitations. JOURNAL OF ORGANIC CHEMISTRY. 2014;79(10):4322–31.
IEEE
[1]
W. Debrouwer, T. Heugebaert, and C. Stevens, “Preparation of tetrasubstituted 3-phosphonopyrroles through hydroamination: scope and limitations,” JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 10, pp. 4322–4331, 2014.
@article{4416082,
  abstract     = {Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines. These starting compounds were obtained in two steps from commercially available beta-ketophosphonates. The method tolerates a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substituents at the 4-position via lithiation or halogenation.},
  author       = {Debrouwer, Wouter and Heugebaert, Thomas and Stevens, Christian},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {INTRAMOLECULAR HYDROAMINATION,:HIGHLY SUBSTITUTED PYRROLES,FUNCTIONALIZED PYRROLES,2-PROPYNYL-1_3-DICARBONYL COMPOUNDS,AMINATION/ANNULATION REACTIONS,INTERMOLECULAR HYDROAMINATION,OLIGOSUBSTITUTED PYRROLES,POLYSUBSTITUTED PYRROLES,CATALYZED HYDROAMINATION,TERMINAL ALKYNES},
  language     = {eng},
  number       = {10},
  pages        = {4322--4331},
  title        = {Preparation of tetrasubstituted 3-phosphonopyrroles through hydroamination: scope and limitations},
  url          = {http://dx.doi.org/10.1021/jo500139z},
  volume       = {79},
  year         = {2014},
}

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