Remote functionalisation via sodium alkylamidozincate intermediates: access to unusual fluorenone and pyridyl ketone reactivity patterns |
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Authors: | Crawford James J Fleming Ben J Kennedy Alan R Klett Jan O'Hara Charles T Orr Samantha A |
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Institution: | AstraZeneca R&D Charnwood, Loughborough, Leicestershire, LE11 5RH, UK. crawford.james@gene.com |
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Abstract: | Treating fluorenone or 2-benzoylpyridine with the sodium zincate (TMEDA)·Na(μ-(t)Bu)(μ-TMP)Zn((t)Bu)] in hexane solution, gives efficient (t)Bu 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. |
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