4.6 Article

Room-Temperature Decarboxylative Couplings of α-Oxocarboxylates with Aryl Halides by Merging Photoredox with Palladium Catalysis

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 38, Pages 13191-13195

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502286

Keywords

CC coupling; decarboxylation; homogeneous catalysis; palladium; photocatalysis

Funding

  1. 973 Program [2012CB215306]
  2. NSFC [21325208, 21172209, 21361140372]
  3. IPDFHCPST [2014FXCX006]
  4. CAS [KJCX2-EW-J02]
  5. FRFCU
  6. PCSIRT

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Enabled by merging iridium photoredox catalysis and palladium catalysis, -oxocarboxylate salts can be decarboxylatively coupled with aryl halides to generate aromatic ketones and amides at room temperature. DFT calculations suggest that this reaction proceeds through a Pd-0-Pd-II-Pd-III pathway, in which the Pd-III intermediate is responsible for reoxidizing Ir-II to complete the Ir-III-*Ir-III-Ir-II photoredox cycle.

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