135227-07-5Relevant academic research and scientific papers
Synthesis of unsymmetrical biaryls via "kinetic" higher order cyanocuprates: Scope, limitations, and spectroscopic insights
Lipshutz, Bruce H.,Siegmann, Konstantin,Garcia, Emiliano,Kayser, Frank
, p. 9276 - 9282 (1993)
Treatment of lower order arylcyanocuprates ArCu(CN)Li with 1 equiv of an aryllithium (Ar′Li) at temperatures around-125°C leads to higher order reagents Ar(Ar′)Cu(CN)Li2. Upon exposure of such reagents at this temperature to ground-state molecular oxygen, good yields of the unsymmetrical biaryl Ar-Ar′ can be realized. Several different types of aryl ligands have been examined, including naphthalenes, to assess the generality of this method. Spectroscopic data (13C NMR) have been obtained on three different cuprates at -130°C and at higher temperatures to determine if their kinetic nature, as illustrated by their synthetic chemistry, can be substantiated by physical means.
Controlled 'decomposition' of "kinetic" higher order cyanocuprates: A new route to unsymmetrical biaryls
Lipshutz, Bruce H.,Seigmann, Konstantin,Garcia, Emiliano
, p. 2579 - 2588 (1992)
By controlling two key reaction parameters (temperature and mode of formation), unprecedented "kinetic" higher order cyanocuprates can be generated. Under oxidative conditins, their chemistry is unique when compared with constitutionally identical reagents formulated in the usual manner. Employing mixed diaryl reagents ArAr′Cu(CN)Li2, prepared from ArLi, Ar′Li, and CuCN, unsymmetrical biaryls (Ar-Ar′) can be realized with remarkable selectivity, in high chemical yields, and in a predicatable fashion.
