Ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage |
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| Authors: | Keisuke KawamotoTakuya Kochi Mitsuo SatoEiichiro Mizushima Fumitoshi Kakiuchi |
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| Affiliation: | a Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
b PRESTO, JST, 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan |
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| 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. |
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| Keywords: | Carbon-fluorine bond cleavage Arylation Ruthenium catalyst Arylboronates Tandem arylation/alkylation |
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