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Synfacts 2023; 19(01): 0059
DOI: 10.1055/s-0042-1753190
Metals in Synthesis

The Murai Reaction: ortho-Directed Ruthenium-Catalyzed C–H Alkylation of Aromatic Ketones

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Phillip Pommerening
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
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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).


 

 

Publication History

Article published online:
16 December 2022

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