TY - JOUR
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
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI Grant Nos. JP17K19126, JP16H04150, and JP15H05839 (Middle Molecular Strategy). T.K. is also grateful for support by JSPS KAKENHI Grant No. JP18H04271 (Precisely Designed Catalysts with Customized Scaffolding). H.K. is also grateful to the Japan Society for the Promotion of Science (JSPS) for a Research Fellowship for Young Scienetists (JP16J02904).
Publisher Copyright:
© 2019 American Chemical Society.
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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U2 - 10.1021/acs.joc.9b01756
DO - 10.1021/acs.joc.9b01756
M3 - Article
C2 - 31533418
AN - SCOPUS:85073193817
VL - 84
SP - 12975
EP - 12982
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -