Arylation of rhodium(II) azavinyl carbenes with boronic acids

Nicklas Selander, Brady T. Worrell, Stepan Chuprakov, Subash Velaparthi, Valery V. Fokin

Research output: Contribution to journalArticle

127 Citations (Scopus)

Abstract

A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized into substituted indoles employing copper catalysis.

Original languageEnglish
Pages (from-to)14670-14673
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number36
DOIs
Publication statusPublished - 12 Sep 2012
Externally publishedYes

Fingerprint

Boronic Acids
Rhodium
Catalysis
Transition metals
Copper
Indoles
Catalysts
Acids
Metals
Temperature
carbene
1-sulfonyl-1,2,3-triazole

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Selander, N., Worrell, B. T., Chuprakov, S., Velaparthi, S., & Fokin, V. V. (2012). Arylation of rhodium(II) azavinyl carbenes with boronic acids. Journal of the American Chemical Society, 134(36), 14670-14673. https://doi.org/10.1021/ja3062453

Arylation of rhodium(II) azavinyl carbenes with boronic acids. / Selander, Nicklas; Worrell, Brady T.; Chuprakov, Stepan; Velaparthi, Subash; Fokin, Valery V.

In: Journal of the American Chemical Society, Vol. 134, No. 36, 12.09.2012, p. 14670-14673.

Research output: Contribution to journalArticle

Selander, N, Worrell, BT, Chuprakov, S, Velaparthi, S & Fokin, VV 2012, 'Arylation of rhodium(II) azavinyl carbenes with boronic acids', Journal of the American Chemical Society, vol. 134, no. 36, pp. 14670-14673. https://doi.org/10.1021/ja3062453
Selander N, Worrell BT, Chuprakov S, Velaparthi S, Fokin VV. Arylation of rhodium(II) azavinyl carbenes with boronic acids. Journal of the American Chemical Society. 2012 Sep 12;134(36):14670-14673. https://doi.org/10.1021/ja3062453
Selander, Nicklas ; Worrell, Brady T. ; Chuprakov, Stepan ; Velaparthi, Subash ; Fokin, Valery V. / Arylation of rhodium(II) azavinyl carbenes with boronic acids. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 36. pp. 14670-14673.
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