Synthesis of 2-Alkenyl-Tethered Anilines

Scott E Denmark, Hyung Min Chi

Research output: Contribution to journalArticle

Abstract

Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N -allylic anilines in the presence of a Lewis acid. The requisite N -allylic anilines were prepared by the addition of vinylmagnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C-N cross-coupling of aryl halides. Taken together, these three strategies allowed access to the requisite aniline substrates with pendant alkenes at the 2-position with excellent trans selectivities.

Original languageEnglish (US)
Pages (from-to)2873-2888
Number of pages16
JournalSynthesis (Germany)
Volume49
Issue number13
DOIs
StatePublished - Jul 3 2017

Fingerprint

Aniline Compounds
Aniline
Styrenes
Lewis Acids
Palladium
Alkenes
Olefins
Styrene
Substrates
Acids

Keywords

  • 2-alkenylanilines
  • 3-aza-Cope rearrangement
  • C-N cross-coupling
  • olefin metathesis
  • trans olefins

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Synthesis of 2-Alkenyl-Tethered Anilines. / Denmark, Scott E; Chi, Hyung Min.

In: Synthesis (Germany), Vol. 49, No. 13, 03.07.2017, p. 2873-2888.

Research output: Contribution to journalArticle

Denmark, Scott E ; Chi, Hyung Min. / Synthesis of 2-Alkenyl-Tethered Anilines. In: Synthesis (Germany). 2017 ; Vol. 49, No. 13. pp. 2873-2888.
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