I2-catalyzed Michael addition of indole and pyrrole to nitroolefins

Chunchi Lin, Jianming Hsu, M. N.V. Sastry, Hulin Fang, Zhijay Tu, Ju Tsung Liu, Yao Ching-Fa

Research output: Contribution to journalArticle

128 Citations (Scopus)

Abstract

An easy and efficient method to generate indolyl nitroalkane 5 and pyrrolyl nitroalkane 7 in high yields using β-nitrostyrene and indole/pyrrole at room temperature in the presence of catalytic amount of iodine is reported. The short reaction times and high yields of product are noteworthy. Molecular iodine promoted Michael addition is operationally simple and efficient method compared to the known Lewis acids or rare earth metal catalysts to generate different indolyl/pyrrolyl nitroalkanes in high yield.

Original languageEnglish
Pages (from-to)11751-11757
Number of pages7
JournalTetrahedron
Volume61
Issue number49
DOIs
Publication statusPublished - 2005 Dec 5

Fingerprint

Pyrroles
Iodine
Rare Earth Metals
Lewis Acids
Catalysts
Temperature
indole

Keywords

  • Indole
  • Iodine
  • Michael addition
  • Pyrrole
  • β-Nitrostyrene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Lin, C., Hsu, J., Sastry, M. N. V., Fang, H., Tu, Z., Liu, J. T., & Ching-Fa, Y. (2005). I2-catalyzed Michael addition of indole and pyrrole to nitroolefins. Tetrahedron, 61(49), 11751-11757. https://doi.org/10.1016/j.tet.2005.09.038

I2-catalyzed Michael addition of indole and pyrrole to nitroolefins. / Lin, Chunchi; Hsu, Jianming; Sastry, M. N.V.; Fang, Hulin; Tu, Zhijay; Liu, Ju Tsung; Ching-Fa, Yao.

In: Tetrahedron, Vol. 61, No. 49, 05.12.2005, p. 11751-11757.

Research output: Contribution to journalArticle

Lin, C, Hsu, J, Sastry, MNV, Fang, H, Tu, Z, Liu, JT & Ching-Fa, Y 2005, 'I2-catalyzed Michael addition of indole and pyrrole to nitroolefins', Tetrahedron, vol. 61, no. 49, pp. 11751-11757. https://doi.org/10.1016/j.tet.2005.09.038
Lin C, Hsu J, Sastry MNV, Fang H, Tu Z, Liu JT et al. I2-catalyzed Michael addition of indole and pyrrole to nitroolefins. Tetrahedron. 2005 Dec 5;61(49):11751-11757. https://doi.org/10.1016/j.tet.2005.09.038
Lin, Chunchi ; Hsu, Jianming ; Sastry, M. N.V. ; Fang, Hulin ; Tu, Zhijay ; Liu, Ju Tsung ; Ching-Fa, Yao. / I2-catalyzed Michael addition of indole and pyrrole to nitroolefins. In: Tetrahedron. 2005 ; Vol. 61, No. 49. pp. 11751-11757.
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AU - Ching-Fa, Yao

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