4.7 Article

Tandem Rh-catalysis: decarboxylative beta-keto acid and alkyne cross-coupling

Journal

CHEMICAL COMMUNICATIONS
Volume 52, Issue 34, Pages 5836-5839

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc02522f

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Funding

  1. UC Irvine
  2. National Institutes of Health [GM105938]
  3. Eli Lilly
  4. NSF Graduate Research Fellowship
  5. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM105938] Funding Source: NIH RePORTER

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Herein, we describe a regioselective Rh-catalyzed decarboxylative cross-coupling of beta-keto acids and alkynes to access branched gamma,delta-unsaturated ketones. Rh-hydride catalysis enables the isomerization of an alkyne to generate ametal-allyl species that can undergo carbon-carbon bond formation. Ketones are generated under mild conditions, without the need for base or activated electrophiles.

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