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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

Rezensent(en):
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
CrossrefPubMedSuche in Google Scholar
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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.


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Review

G. Evano, C. Theunissen Angew. Chem. Int. Ed. 2019, 58, 7202–7236.


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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).


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Publikationsverlauf

Artikel online veröffentlicht:
16. Dezember 2022

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