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.
| Language | English |
|---|---|
| Pages | 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
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Remote functionalisation via sodium alkylamidozincate intermediates : access to unusual fluorenone and pyridyl ketone reactivity patterns. / Crawford, James J.; Fleming, Ben J.; Kennedy, Alan R.; Klett, Jan; O'Hara, Charles T.; Orr, Samantha A.
In: Chemical Communications (London), Vol. 47, No. 13, 11.01.2011, p. 3772-3774.Research output: Contribution to journal › Article
TY - JOUR
T1 - Remote functionalisation via sodium alkylamidozincate intermediates
T2 - Chemical Communications (London)
AU - Crawford, James J.
AU - Fleming, Ben J.
AU - Kennedy, Alan R.
AU - Klett, Jan
AU - O'Hara, Charles T.
AU - Orr, Samantha A.
PY - 2011/1/11
Y1 - 2011/1/11
N2 - 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.
AB - 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.
KW - metal-mediated zincation
KW - ferroelectric liquid-crystals
KW - directed ortho-metalation
KW - tertiary aromatic amide
KW - structural insights
KW - polar order
KW - 1,4-dihydropyridines
KW - magnesiation
KW - derivatives
KW - complexes
U2 - 10.1039/c1cc10193e
DO - 10.1039/c1cc10193e
M3 - Article
VL - 47
SP - 3772
EP - 3774
JO - Chemical Communications (London)
JF - Chemical Communications (London)
SN - 0009-241X
IS - 13
ER -