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 language | English |
|---|---|
| Pages (from-to) | 3772-3774 |
| Number of pages | 3 |
| Journal | Chemical Communications (London) |
| Volume | 47 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 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
Cite this
Crawford, J. J., Fleming, B. J., Kennedy, A. R., Klett, J., O'Hara, C. T., & Orr, S. A. (2011). Remote functionalisation via sodium alkylamidozincate intermediates: access to unusual fluorenone and pyridyl ketone reactivity patterns. Chemical Communications (London), 47(13), 3772-3774. https://doi.org/10.1039/c1cc10193e