4.7 Article

Selective Synthesis of o-Acylbenzylphosphonates by Insertion Reactions of Arynes into β-Ketophosphonates

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 15, Pages 5691-5694

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo900847u

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Funding

  1. New Century Excellent Talents in University [NCET-06-0711]
  2. Hunan Provincial Education Department [08B053, 08A037]
  3. KLCBTCMR [KLCBTCMR2008-11]
  4. Hunan Normal University [080605]
  5. National Natural Science Foundation of China [20872112]

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A mild method for selective synthesis of o-acylbenzylphosphonates has been developed by the reactions of arynes with beta-ketophosphonates. In the presence of CsF and THF, the carbon-carbon sigma-bonds of 2-oxopropylphosphonates were selectively cleaved and added to arynes providing the corresponding 2-acylbenzylphosphonates in moderate to good yields.

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