134869-91-3Relevant academic research and scientific papers
Transition-Metal-Free Cross-Coupling of Aryl and N-Heteroaryl Cyanides with Benzylic Zinc Reagents
Quinio, Pauline,Roman, Daniela Sustac,León, Thierry,William, Sharankini,Karaghiosoff, Konstantin,Knochel, Paul
, p. 4396 - 4399 (2015)
Functionalized 4-benzylated pyridines can be efficiently prepared by a transition-metal-free cross-coupling between various benzylic zinc chlorides and substituted 4-cyanopyridines in THF/DMPU under microwave irradiation (40 °C, 0.5-1.5 h). Selective benzylations on polycyano-aromatics have also been achieved under these mild conditions. We also report a novel oxidative nucleophilic substitution of a hydrogen on 1,3-dicyanobenzene using benzylic zinc reagents.
Orientation and alkylation effects on cation-π interactions in aqueous solution
Rashkin, Mark J.,Hughes, Robert M.,Calloway, Nathaniel T.,Waters, Marcey L.
, p. 13320 - 13325 (2007/10/03)
We have investigated the orientation dependence of the cation-π interaction between a phenyl ring and a pyridinium ring in the context of a flexible model system in water. Of the four possible positions of the pyridinium nitrogen, ipso, ortho, meta, and para, we found a variation in the interaction energy of about 0.75 kcal mol-1, with the stacking of the ipso-pyridinium ring providing the strongest interaction. The observed stability is attributed to the maximization of the electrostatic interaction, minimization of rotamers, and possible differences in hydration phenomena arising from alkylation.
A facile synthesis of functionalized 4-benzylpyridines by using mixed copper, zinc benzylic organometallics
Chia,Shiao
, p. 2033 - 2034 (2007/10/02)
A general approach by use of highly functionalized mixed copper zinc, benzylic organometallics to react with N-ethoxycarbonylpyridinium chloride to give regioselectively 4-benzylpyridines after oxygen oxidation in 30-75% yield is described.
