777097-55-9Relevant academic research and scientific papers
Synthesis and deprotonation of 2-(halophenyl)pyridines and 1-(halophenyl)isoquinolines
Mongin, Florence,Rebstock, Anne-Sophie,Trecourt, Francois,Queguiner, Guy,Marsais, Francis
, p. 6766 - 6771 (2004)
The ability of the 2-pyridyl and 1-isoquinolyl groups to direct metalation was studied in the benzene series. For this purpose, 2-(halophenyl)pyridines and 1-(halophenyl)isoquinolines were prepared. Interestingly, nucleophilic addition reactions on the azine ring were not observed under kinetic control using butyllithium, and the substrates were cleanly deprotonated on the benzene ring: the azine ring acidifies the adjacent hydrogen H2 (N-H2 interaction through space and/or inductive electron-withdrawing effect) and probably favors the approach of butyllithium (chelation). Under thermodynamic conditions using lithium dialkylamides, the presence of the azine group makes the lithio derivative at C2′ more stable (chelation and/or inductive electron-withdrawing effect). This was evidenced in two ways: (1) syntheses of 2-halophenyllithiums (F, Cl, Br) substituted at C6 by a 2-pyridyl or 1-isoquinolyl group without elimination of lithium halide and (2) iodine migration from C2′ to C4′ when treating 2-(3-halo-2-iodophenyl) pyridines or 1-(3-fluoro-2-iodophenyl)isoquinoline with LTMP. Comparisons between the 2-pyridyl and fluoro units showed the latter was the stronger directing group for deprotonation.
Metal complexes
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, (2008/06/13)
The present invention describes new types of metal complexes. Such compounds can be used as functional materials in a series of different types of applications which can be classified within the electronics industry in the widest sense. The inventive comp
