Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives

Tetsuro Koreeda; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1016/j.jorganchem.2013.06.001

Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives

Tetsuro Koreeda, Takuya Kochi, Fumitoshi Kakiuchi

Department of Chemistry

Research output: Contribution to journal › Article

20 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 language	English
Pages (from-to)	148-152
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	741-742
Issue number	1
DOIs	https://doi.org/10.1016/j.jorganchem.2013.06.001
Publication status	Published - 2013 Jan 1

Keywords

Carbonenitrogen bond cleavage
Deamination
Ruthenium catalyst
Tandem deamination/alkylation

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2013.06.001

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Koreeda, T., Kochi, T., & Kakiuchi, F. (2013). Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives. Journal of Organometallic Chemistry, 741-742(1), 148-152. https://doi.org/10.1016/j.jorganchem.2013.06.001

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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.",

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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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KW - Ruthenium catalyst

KW - Tandem deamination/alkylation

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