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

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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.;
CORE (COnnecting REpositories)