title: Remote functionalisation via sodium alkylamidozincate intermediates: access to unusual fluorenone and pyridyl ketone reactivity patterns.
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.
authors.affiliation: AstraZeneca R&D Charnwood, Loughborough, Leicestershire, LE11 5RH, UK. crawford.james@gene.com
authors.forename: James J
authors.initials: JJ
authors.lastname: Crawford
authors.forename: Ben J
authors.initials: BJ
authors.lastname: Fleming
authors.forename: Alan R
authors.initials: AR
authors.lastname: Kennedy
authors.forename: Jan
authors.initials: J
authors.lastname: Klett
authors.forename: Charles T
authors.initials: CT
authors.lastname: O'Hara
authors.forename: Samantha A
authors.initials: SA
authors.lastname: Orr
mesh_terms: D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D005449:Fluorenes; D007659:Ketones; C559521:Na(mu-(t)Bu)(mu-TMP)Zn((t)Bu); D009942:Organometallic Compounds; D011725:Pyridines