Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 23, Pages 5884-5888Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201900582
Keywords
alkynylation; decarboxylation; enolates; ketones; palladium
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Funding
- MEXT [16H06593]
- JST ACT-C Grant [JPMJCR12YM]
- Grants-in-Aid for Scientific Research [16H06593] Funding Source: KAKEN
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Palladium-catalyzed decarboxylative alkynylation of alpha-acyloxyketones triggered by C(sp(3))-O bond cleavage is disclosed. The decarboxylation strategy featuring a neutral reaction condition enabled an unprecedent catalytic alkynylation of a ketone enolate. The reaction was applied to a variety of substrates, giving desired products in good yields. We successfully obtained X-ray crystallography of a new palladium-enolate intermediate that was synthesized by a reaction of [Pd(cod)(CH2TMS)(2)] with XPhos and alpha-acyloxyketone at room temperature, indicating facile C(sp(3))-O bond disconnection.
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