Selective Monoarylation of Aromatic Ketones via C-H Bond Cleavage by Trialkylphosphine Ruthenium Catalysts

Issei Suzuki; Hikaru Kondo; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1021/acs.joc.9b01756

Selective Monoarylation of Aromatic Ketones via C-H Bond Cleavage by Trialkylphosphine Ruthenium Catalysts

Issei Suzuki, Hikaru Kondo, Takuya Kochi, Fumitoshi Kakiuchi

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

A catalyst system consisting of RuHCl(CO)(PⁱPr₃)₂, CsF, and a styrene derivative was found to be applicable to selective monoarylation of aromatic ketones via ortho C-H bond cleavage. The reaction of 2′-methoxyacetophenone with arylboronates gave C-H arylation products without cleaving the ortho C-O bond. Acetophenone was also converted to monoarylation products with high selectivity. Cyclohexanone was found to be an effective solvent for the C-H arylation using the catalyst system.

Original language	English
Pages (from-to)	12975-12982
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	84
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.9b01756
Publication status	Published - 2019 Oct 18

ASJC Scopus subject areas

Organic Chemistry

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title = "Selective Monoarylation of Aromatic Ketones via C-H Bond Cleavage by Trialkylphosphine Ruthenium Catalysts",

abstract = "A catalyst system consisting of RuHCl(CO)(PiPr3)2, CsF, and a styrene derivative was found to be applicable to selective monoarylation of aromatic ketones via ortho C-H bond cleavage. The reaction of 2′-methoxyacetophenone with arylboronates gave C-H arylation products without cleaving the ortho C-O bond. Acetophenone was also converted to monoarylation products with high selectivity. Cyclohexanone was found to be an effective solvent for the C-H arylation using the catalyst system.",

author = "Issei Suzuki and Hikaru Kondo and Takuya Kochi and Fumitoshi Kakiuchi",

year = "2019",

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journal = "Journal of Organic Chemistry",

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T1 - Selective Monoarylation of Aromatic Ketones via C-H Bond Cleavage by Trialkylphosphine Ruthenium Catalysts

AU - Suzuki, Issei

AU - Kondo, Hikaru

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

PY - 2019/10/18

Y1 - 2019/10/18

N2 - A catalyst system consisting of RuHCl(CO)(PiPr3)2, CsF, and a styrene derivative was found to be applicable to selective monoarylation of aromatic ketones via ortho C-H bond cleavage. The reaction of 2′-methoxyacetophenone with arylboronates gave C-H arylation products without cleaving the ortho C-O bond. Acetophenone was also converted to monoarylation products with high selectivity. Cyclohexanone was found to be an effective solvent for the C-H arylation using the catalyst system.

AB - A catalyst system consisting of RuHCl(CO)(PiPr3)2, CsF, and a styrene derivative was found to be applicable to selective monoarylation of aromatic ketones via ortho C-H bond cleavage. The reaction of 2′-methoxyacetophenone with arylboronates gave C-H arylation products without cleaving the ortho C-O bond. Acetophenone was also converted to monoarylation products with high selectivity. Cyclohexanone was found to be an effective solvent for the C-H arylation using the catalyst system.

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