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 › peer-review

26 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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title = "Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives",

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.",

keywords = "Carbonenitrogen bond cleavage, Deamination, Ruthenium catalyst, Tandem deamination/alkylation",

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T1 - Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives

AU - Koreeda, Tetsuro

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

PY - 2013/1/1

Y1 - 2013/1/1

N2 - 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.

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.

KW - Carbonenitrogen bond cleavage

KW - Deamination

KW - Ruthenium catalyst

KW - Tandem deamination/alkylation

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DO - 10.1016/j.jorganchem.2013.06.001

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VL - 741-742

SP - 148

EP - 152

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 1

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Ruthenium-catalyzed reductive deamination and tandem alkylation of aniline derivatives

Abstract

Keywords

ASJC Scopus subject areas

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