37581-19-4Relevant academic research and scientific papers
Synthesis of 4-benzylpyridines via Pd-catalyzed CH3-arylation of 4-picoline
Wu, Jing,Wang, Dadian,Chen, Xiang,Gui, Qingwen,Li, Hua,Tan, Ze,Huang, Genping,Wang, Guangwei
supporting information, p. 7509 - 7512 (2017/09/27)
A highly efficient synthesis of 4-benzylpyridines was developed via Pd-catalyzed C(sp3)-H arylation between 4-picoline and aryl halides. It was found that the best yields were achieved with a simple Pd(PPh3)4 catalyst and Cs2CO3 as the base. Compared with the known methods, our reaction does not require the use of a strong organometallic reagent as the base.
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
supporting information, p. 4396 - 4399 (2015/09/15)
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.
Lewis acid promoted benzylic cross-couplings of pyridines with aryl bromides
Duez, Stephanie,Steib, Andreas K.,Manolikakes, Sophia M.,Knochel, Paul
supporting information; experimental part, p. 7686 - 7690 (2011/10/17)
Either ZnCl2, Sc(OTf)3, or BF3OEt 2 can promote the palladium-catalyzed arylation of methylpyridines and related heterocycles (see example). The complexation of the Lewis acid to the nitrogen atom in the heteroc
Convenient, benign and scalable synthesis of 2- and 4-substituted benzylpiperidines
Agai, Bela,Proszenyak, Agnes,Tarkanyi, Gabor,Vida, Laszlo,Faigl, Ferenc
, p. 3623 - 3632 (2007/10/03)
A short, scalable and environmentally benign synthesis of 2- and 4-substituted benzylpiperidines has been developed. The method is based on the temperature-programmed consecutive deoxygenation and heteroaromatic ring saturation of aryl(pyridin-2-yl)- and aryl(pyridin-4-yl)methanols and aryl(pyridin-4-yl)methanones in the presence of Pd/C catalyst. The crucial roles of the temperature, the acidity and the substrate structure in the change of selectivity have been demonstrated by isolation of several substituted aryl(piperidine)methanols. The carbinols and ketones were prepared from commercially available pyridinecarbaldehydes or 4-cyanopyridine and substituted bromobenzenes via organometallic intermediates. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
