4.6 Article

Copper-Catalyzed One-Pot Denitrogenative-Dehydrogenative-Decarboxylative Coupling of β-Ketoacids with Trifluorodiazoethane: Facile Access to Trifluoromethylated Aldol Products

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 27, Pages 8325-8329

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403073

Keywords

2,2,2-trifluorodiazoethane; decarboxylation; dehydrogenation cross-coupling reaction; enantioselectivity; beta-ketoacids

Funding

  1. National Natural Science Foundation of China [21172170, 21225208]
  2. National Basic Research Program of China (973 Program) [2014CB745100]

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A novel copper-catalyzed one-pot cross-coupling of beta-ketoacids with in situ generated trifluorodiazoethane has been developed. This reaction provides a direct and efficient method, in which one C-C bond and one C-O bond were formed in a carbenoid center with concomitant denitrogenation-dehydrogenation-decarboxylation, to afford trifluoromethylated aldol products. In several preliminary experiments, good to high enantioselectivities were also obtained.

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