Murai S,
*,
Kakiuchi F,
Sekine S,
Tanaka Y,
Kamatani A,
Sonoda M,
Chatani N.
Osaka University, Japan
Efficient Catalytic Addition of Aromatic Carbon–Hydrogen Bonds to Olefins.
Nature 1993;
366: 529-531
DOI:
10.1038/366529a0
Key words
alkenes - aryl ketones - C–H activation - directed C–H alkylation - ruthenium catalysis
Significance
In 1993, the Murai group reported a highly efficient ruthenium(0)-catalyzed ortho-C–H alkylation of aromatic and heteroaromatic ketones with various alkenes.
Review
G. Evano, C. Theunissen Angew. Chem. Int. Ed.
2019, 58, 7202–7236.
Comment
In this transformation, the carbonyl group serves as a directing group. The chelating
effect leads to a five-membered metallocycle intermediate, which is crucial for the
reaction. DFT calculations by Koga and Morokuma support the shown mechanism (J. Am. Chem. Soc.
1998, 120, 12692).
