Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 21, Pages 3725-3729Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200765
Keywords
ruthenium hydride catalyst; cross-coupling; 1,3-diaryl 1,3-diketone; beta-Ru ketone complex
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Funding
- JSPS
- Center for Emergent Functional Matter Science at NYCU
- [MOST-108-2113-M-009-007]
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The RuHCl(CO)(PPh3)(3)-catalyzed cross-coupling reaction has been extended to synthesize 1,3-diaryl 1,3-diketones, and also applied to the synthesis of PPT (propyl pyrazole triol). A study revealed the formation of a five-membered ruthenacycle, beta-ruthenium ketone, during the reaction.
RuHCl(CO)(PPh3)(3)-catalyzed cross-coupling of alkenyl ketones with aldehydes has been extended to the synthesis of 1,3-diaryl 1,3-diketones. The reaction has been successfully applied to the synthesis of PPT (propyl pyrazole triol), a selective estrogen receptor modulator compound. A study of the stoichiometric reaction of phenyl vinyl ketone with RuHCl(CO)(PPh3)(3) has revealed that the beta-ruthenium ketone PhCOCH2CH2RuCl(CO)(PPh3)(2), a five-membered ruthenacycle is formed with liberation of one molecule of PPh3. The observed catalytic activity of this ruthenacycle in the presence of PPh3 suggests that it serves as a resting state, in equilibrium with an oxa-pi-allyl ruthenium species, which is the key coupling partner with aldehyde substrates.
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