Ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage

Keisuke Kawamoto; Takuya Kochi; Mitsuo Sato; Eiichiro Mizushima; Fumitoshi Kakiuchi

doi:10.1016/j.tetlet.2011.09.005

Ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage

Keisuke Kawamoto, Takuya Kochi, Mitsuo Sato, Eiichiro Mizushima, Fumitoshi Kakiuchi

Department of Chemistry

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

28 Citations (Scopus)

Abstract

We report here ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage. In the presence of trimethylvinylsilane and cesium fluoride, ortho carbon-fluoride bonds of aromatic ketones were phenylated by 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane using RuH₂(CO)(PPh₃)₃ as a catalyst. Tandem C-F phenylation/C-H alkylation was observed for substrates bearing both one ortho hydrogen and one ortho fluorine atoms

Original language	English
Pages (from-to)	5888-5890
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2011.09.005
Publication status	Published - 2011 Nov 2

Keywords

Arylation
Arylboronates
Carbon-fluorine bond cleavage
Ruthenium catalyst
Tandem arylation/alkylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.09.005

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title = "Ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage",

abstract = "We report here ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage. In the presence of trimethylvinylsilane and cesium fluoride, ortho carbon-fluoride bonds of aromatic ketones were phenylated by 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane using RuH2(CO)(PPh3)3 as a catalyst. Tandem C-F phenylation/C-H alkylation was observed for substrates bearing both one ortho hydrogen and one ortho fluorine atoms",

keywords = "Arylation, Arylboronates, Carbon-fluorine bond cleavage, Ruthenium catalyst, Tandem arylation/alkylation",

author = "Keisuke Kawamoto and Takuya Kochi and Mitsuo Sato and Eiichiro Mizushima and Fumitoshi Kakiuchi",

note = "Funding Information: This work was supported, in part, by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan and by The Science Research Promotion Fund .",

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doi = "10.1016/j.tetlet.2011.09.005",

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T1 - Ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage

AU - Kawamoto, Keisuke

AU - Kochi, Takuya

AU - Sato, Mitsuo

AU - Mizushima, Eiichiro

AU - Kakiuchi, Fumitoshi

N1 - Funding Information: This work was supported, in part, by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan and by The Science Research Promotion Fund .

PY - 2011/11/2

Y1 - 2011/11/2

N2 - We report here ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage. In the presence of trimethylvinylsilane and cesium fluoride, ortho carbon-fluoride bonds of aromatic ketones were phenylated by 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane using RuH2(CO)(PPh3)3 as a catalyst. Tandem C-F phenylation/C-H alkylation was observed for substrates bearing both one ortho hydrogen and one ortho fluorine atoms

AB - We report here ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage. In the presence of trimethylvinylsilane and cesium fluoride, ortho carbon-fluoride bonds of aromatic ketones were phenylated by 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane using RuH2(CO)(PPh3)3 as a catalyst. Tandem C-F phenylation/C-H alkylation was observed for substrates bearing both one ortho hydrogen and one ortho fluorine atoms

KW - Arylation

KW - Arylboronates

KW - Carbon-fluorine bond cleavage

KW - Ruthenium catalyst

KW - Tandem arylation/alkylation

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DO - 10.1016/j.tetlet.2011.09.005

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SN - 0040-4039

VL - 52

SP - 5888

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage

Abstract

Keywords

ASJC Scopus subject areas

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