Synthesis of α-diketones from alkylaryl- and diarylalkynes using mercuric salts

Org Lett. 2014 Apr 18;16(8):2142-5. doi: 10.1021/ol500592m. Epub 2014 Apr 1.

Abstract

Both alkylarylalkynes and diarylalkynes 1 are converted into the α-diketones 2 in good yield by the use of mercuric salts, e.g., mercuric nitrate hydrate or mercuric triflate, in the presence of water. Other mercuric salts, e.g., sulfate, chloride, acetate, or trifluoroacetate, do not provide the diketone product. A possible mechanism is proposed.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Mercury / chemistry*
  • Mercury Compounds / chemistry
  • Mesylates / chemistry
  • Molecular Structure
  • Nitrates / chemistry
  • Oxidation-Reduction
  • Salts
  • Water

Substances

  • Alkynes
  • Ketones
  • Mercury Compounds
  • Mesylates
  • Nitrates
  • Salts
  • mercuric triflate
  • Water
  • mercury nitrate
  • Mercury