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Synlett 2001; 2001(10): 1535-1538
DOI: 10.1055/s-2001-17471
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Regioselective C-Acylation of Vinylphosphorus Compounds Through Electroreduction or Mg-Promoted Reduction

Makoto Kyoda* , Takamichi Yokoyama, Hirofumi Maekawa, Toshinobu Ohno, Ikuzo Nishiguchi
  • *Department of Chemistry, Nagaoka University of Technology, 1603-1, Kamitomioka-cho, Nagaoka, Niigata 940-2188, Japan; Fax + 81(258)47 93 00; E-mail: nishiiku@vos.nagaokaut.ac.jp
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Publication Date:
27 September 2001 (online)

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Either of electroreduction or Mg-promoted electron-transfer reaction of vinylphosphonate derivatives 1-4 in the presence of acid anhydrides 5 a - c or acid chlorides 15 b, c brought about regioselective C-acylation to give the corresponding β-acylphosphonates 3 in good yields. The reaction may be initiated through one-electron transfer from either a cathode or Mg metal to a substrate to give the corresponding anion radical, which is then subjected to electrophilic attack of an acylating agent, followed by the fast second electron-transfer.

vinylphosphonates - electron-transfer - acylations - magnesium - cross-coupling