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

Crawford, James J. and Fleming, Ben J. and Kennedy, Alan R. and Klett, Jan and O'Hara, Charles T. and Orr, Samantha A. (2011) Remote functionalisation via sodium alkylamidozincate intermediates : access to unusual fluorenone and pyridyl ketone reactivity patterns. Chemical Communications (London), 47 (13). pp. 3772-3774. ISSN 0009-241X (https://doi.org/10.1039/c1cc10193e)

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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.

ORCID iDs

Crawford, James J., Fleming, Ben J. ORCID logoORCID: https://orcid.org/0000-0003-0111-8679, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Klett, Jan, O'Hara, Charles T. and Orr, Samantha A.;
  • Item type:Article
    ID code:33243
    Dates:
    Date
    Event
    11 January 2011
    Published
    Keywords:metal-mediated zincation, ferroelectric liquid-crystals, directed ortho-metalation, tertiary aromatic amide, structural insights, polar order, 1,4-dihydropyridines, magnesiation, derivatives, complexes, Chemistry, Chemistry(all)
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:14 Sep 2011 15:09
    Last modified:17 Nov 2023 01:51
    URI:https://strathprints.strath.ac.uk/id/eprint/33243
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