4.8 Article

Tandem reaction of 1,2-allenic ketone with alpha-halo ketone or alpha-halo ester in water: an efficient and sustainable synthesis of 1,3,4 '-tricarbonyl compounds

Journal

GREEN CHEMISTRY
Volume 13, Issue 11, Pages 3218-3223

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c1gc15707h

Keywords

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Funding

  1. Natural Science Foundation of China [20972042, 20911140238]
  2. Innovation Scientists and Technicians Troop Construction Projects of Henan Province [104100510019]
  3. PCSIRT [IRT1061]

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An efficient and sustainable synthesis of the otherwise difficult to obtain 1,3,4'-tricarbonyl compounds through a water mediated, TBAF center dot 3H(2)O promoted unprecedented tandem reaction of 1,2-allenic ketone with alpha-halo ketone or alpha-halo ester has been developed. Remarkably enhanced reactivity and improved chemoselectivity by using water as the reaction medium was observed. The 1,3,4'-tricarbonyl compounds facilitate further versatile transformations, which underscores the importance of these products as synthetic intermediates.

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