Double C-H functionalization in sequential order: Direct synthesis of polycyclic compounds by a palladium-catalyzed C-H alkenylation-arylation cascade

Hiroaki Ohno, Mutsumi Iuchi, Naoto Kojima, Takehiko Yoshimitsu, Nobutaka Fujii, Tetsuaki Tanaka

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Palladium-catalyzed cascade C-H alkenylation and arylation provides convenient access to polycyclic aromatic compounds. Treatment of 3-bromoaniline derivatives bearing a bromocinnamyl group on the nitrogen atom with a catalytic amount of [Pd(OAc) 2] and PCy 3âHBF 4 in the presence of Cs 2CO 3 in dioxane affords naphthalene-fused indole derivatives in good yields. This double cyclization reaction is also applicable to heterocyclic substrates, giving fused indoles containing a heteroaromatic ring such as dibenzofuran, dibenzothiophene, carbazole, indole, or benzofuran through heterocyclic C-H arylation. When using a 2,6-unsubstituted aniline derivative, the first C-H arylation preferentially proceeds at the more hindered position of the aniline ring.

Original languageEnglish
Pages (from-to)5352-5360
Number of pages9
JournalChemistry - A European Journal
Volume18
Issue number17
DOIs
Publication statusPublished - Apr 23 2012
Externally publishedYes

Fingerprint

Alkenylation
Polycyclic Compounds
Palladium
Aniline
Derivatives
Bearings (structural)
Indoles
Aromatic compounds
Cyclization
Naphthalene
Nitrogen
Atoms
Substrates
aniline
indole

Keywords

  • C-H bond activation
  • domino reactions
  • heterocycles
  • palladium
  • polycycles

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Double C-H functionalization in sequential order : Direct synthesis of polycyclic compounds by a palladium-catalyzed C-H alkenylation-arylation cascade. / Ohno, Hiroaki; Iuchi, Mutsumi; Kojima, Naoto; Yoshimitsu, Takehiko; Fujii, Nobutaka; Tanaka, Tetsuaki.

In: Chemistry - A European Journal, Vol. 18, No. 17, 23.04.2012, p. 5352-5360.

Research output: Contribution to journalArticle

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