Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

We developed two new catalytic transformations of anilines via oxidative addition of CeN bonds to ruthenium centers. One is ruthenium-catalyzed reductive deaminatoindeamination of N-alkylated oacylanilines. The other one is catalytic coupling of N-alkylated o-acylanilines with olefins giving orthoalkylated aromatic ketones via CeN bond cleavage. This reaction involves a ruthenium hydride species as an intermediate, formed after b-hydride elimination from the ruthenium amide species.

Original languageEnglish
Pages (from-to)148-152
Number of pages5
JournalJournal of Organometallic Chemistry
Volume741-742
Issue number1
DOIs
Publication statusPublished - 2013

Fingerprint

Deamination
Ruthenium
alkylation
Alkylation
Aniline
aniline
ruthenium
Derivatives
Hydrides
hydrides
Aniline Compounds
Alkenes
Ketones
Amides
ketones
amides
alkenes
Olefins
cleavage
elimination

Keywords

  • Carbonenitrogen bond cleavage
  • Deamination
  • Ruthenium catalyst
  • Tandem deamination/alkylation

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Biochemistry

Cite this

Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives. / Koreeda, Tetsuro; Kochi, Takuya; Kakiuchi, Fumitoshi.

In: Journal of Organometallic Chemistry, Vol. 741-742, No. 1, 2013, p. 148-152.

Research output: Contribution to journalArticle

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AB - We developed two new catalytic transformations of anilines via oxidative addition of CeN bonds to ruthenium centers. One is ruthenium-catalyzed reductive deaminatoindeamination of N-alkylated oacylanilines. The other one is catalytic coupling of N-alkylated o-acylanilines with olefins giving orthoalkylated aromatic ketones via CeN bond cleavage. This reaction involves a ruthenium hydride species as an intermediate, formed after b-hydride elimination from the ruthenium amide species.

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