Remote functionalisation via sodium alkylamidozincate intermediates: access to unusual fluorenone and pyridyl ketone reactivity patterns

James J. Crawford, Ben J. Fleming, Alan R. Kennedy, Jan Klett, Charles T. O'Hara, Samantha A. Orr

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Abstract

Treating fluorenone or 2-benzoylpyridine with the sodium zincate [(TMEDA)center dot Na(mu-Bu-t)(mu-TMP)Zn(Bu-t)] in hexane solution, gives efficient Bu-t addition across the respective organic substrate in a highly unusual 1,6-fashion, producing isolable organometallic intermediates which can be quenched and aerobically oxidised to give 3-tert-butyl-9H-fluoren-9-one and 2-benzoyl-5-tert-butylpyridine respectively.

Original languageEnglish
Pages (from-to)3772-3774
Number of pages3
JournalChemical Communications (London)
Volume47
Issue number13
DOIs
Publication statusPublished - 11 Jan 2011

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Keywords

  • metal-mediated zincation
  • ferroelectric liquid-crystals
  • directed ortho-metalation
  • tertiary aromatic amide
  • structural insights
  • polar order
  • 1,4-dihydropyridines
  • magnesiation
  • derivatives
  • complexes

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