One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

Takafumi Kitawaki, Yoko Hayashi, Akiko Ueno, Noritaka Chida

Research output: Contribution to journalArticle

90 Citations (Scopus)

Abstract

The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2′-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented.

Original languageEnglish
Pages (from-to)6792-6801
Number of pages10
JournalTetrahedron
Volume62
Issue number29
DOIs
Publication statusPublished - 2006 Jul 17

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Carbazoles
Palladium
Amines
Alkaloids
murrastifoline-A

Keywords

  • Double N-arylation
  • Murrastifoline-A
  • N-Substituted carbazole
  • One-pot synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A. / Kitawaki, Takafumi; Hayashi, Yoko; Ueno, Akiko; Chida, Noritaka.

In: Tetrahedron, Vol. 62, No. 29, 17.07.2006, p. 6792-6801.

Research output: Contribution to journalArticle

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