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Oxidative coupling of indoles using thallium(III) trifluoroacetate

Journal Article


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Abstract


  • The oxidative coupling of polysubstituted electron-rich indoles mediated by thallium trifluoroacetate was found to be a facile, clean, and high yielding reaction. Indolic coupling sites were determined by the nature of the substituents present, with dimerisation at the indole 2-position being the dominant outcome. Indoles bearing two potential reaction sites with similar reactivity were additionally found to undergo heterocoupling.

Authors


  •   Keller, Paul A.
  •   Yepuri, Rao (external author)
  •   Kelso, Michael J.
  •   Mariani, Michael (external author)
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)

Publication Date


  • 2008

Citation


  • Keller, P. A., Yepuri, N., Kelso, M. J., Mariani, M., Skelton, B. W. & White, A. H. (2008). Oxidative coupling of indoles using thallium(III) trifluoroacetate. Tetrahedron, 64 (33), 7787-7795.

Scopus Eid


  • 2-s2.0-46149104710

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1177&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/151

Number Of Pages


  • 8

Start Page


  • 7787

End Page


  • 7795

Volume


  • 64

Issue


  • 33

Abstract


  • The oxidative coupling of polysubstituted electron-rich indoles mediated by thallium trifluoroacetate was found to be a facile, clean, and high yielding reaction. Indolic coupling sites were determined by the nature of the substituents present, with dimerisation at the indole 2-position being the dominant outcome. Indoles bearing two potential reaction sites with similar reactivity were additionally found to undergo heterocoupling.

Authors


  •   Keller, Paul A.
  •   Yepuri, Rao (external author)
  •   Kelso, Michael J.
  •   Mariani, Michael (external author)
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)

Publication Date


  • 2008

Citation


  • Keller, P. A., Yepuri, N., Kelso, M. J., Mariani, M., Skelton, B. W. & White, A. H. (2008). Oxidative coupling of indoles using thallium(III) trifluoroacetate. Tetrahedron, 64 (33), 7787-7795.

Scopus Eid


  • 2-s2.0-46149104710

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1177&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/151

Number Of Pages


  • 8

Start Page


  • 7787

End Page


  • 7795

Volume


  • 64

Issue


  • 33