5558-31-6Relevant articles and documents
Cu-Catalyzed alkylation-cyanation type difunctionalization of styrenes with aliphatic aldehydes and TMSCN via decarbonylation
Zhou, Yu-Ling,Chen, Jun-Jia,Cheng, Jing,Yang, Luo
supporting information, p. 1231 - 1235 (2022/02/19)
A copper-catalyzed decarbonylative alkylation-cyanation of styrene derivatives with aliphatic aldehydes and trimethylsilyl cyanide to provide chain elongated nitriles is reported. Using TBHP as an oxidant and free radical initiator, the reaction can smoothly convert abundant α-di-substituted, α-mono-substituted and linear aliphatic aldehydes into the corresponding 3°, 2° and 1° alkyl radicals to initiate the subsequent radical-type difunctionalization of various styrenes.
Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis
Borghs, Jannik C.,Tran, Mai Anh,Sklyaruk, Jan,Rueping, Magnus,El-Sepelgy, Osama
, p. 7927 - 7935 (2019/06/24)
A general and chemoselective catalytic alkylation of nitriles using a homogeneous nonprecious manganese catalyst is presented. This alkylation reaction uses naturally abundant alcohols and readily available nitriles as coupling partners. The reaction tolerates a wide range of functional groups and heterocyclic moieties, efficiently providing useful cyanoalkylated products with water as the only side product. Importantly, methanol can be used as a C1 source and the chemoselective C-methylation of nitriles is achieved. The mechanistic investigations support the multiple role of the metal-ligand manganese catalyst, the dehydrogenative activation of the alcohol, α-C-H activation of the nitrile, and hydrogenation of the in-situ-formed unsaturated intermediate.
Environmentally friendly one-pot synthesis of α-alkylated nitriles using hydrotalcite-supported metal species as multifunctional solid catalysts
Motokura, Ken,Fujita, Noriaki,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Jitsukawa, Koichiro,Kaneda, Kiyotomi
, p. 8228 - 8239 (2007/10/03)
A ruthenium-grafted hydrotalcite (Ru/HT) and hydrotalcite-supported palladium nanoparticles (Pdnano/ HT) are easily prepared by treating basic layered double hydroxide, hydrotalcite (HT, Mg6Al 2(OH)16CO3) with aqueous RuCl 3·n H2O and K2[PdCl4] solutions, respectively, using surface impregnation methods. Analysis by means of X-ray diffraction, and energydispersive X-ray, electron paramagnetic resonance, and X-ray absorption fine structure spectroscopies proves that a monomeric RuIV species is grafted onto the surface of the HT. Meanwhile, after reduction of a surface-isolated PdII species, highly dispersed Pd nanoclusters with a mean diameter of about 70 A is observed on the Pdnano/HT surface by transmission electron microscopy analysis. These hydrotalcite-supported metal catalysts can effectively promote α-alkylation reactions of various nitriles with primary alcohols or carbonyl compounds through tandem reactions consisting of metal-catalyzed oxidation and reduction, and an aldol reaction promoted by the base sites of the HT. In these catalytic α-alkylations, homogeneous bases are unnecessary and the only by-product is water. Additionally, these catalyst systems are applicable to one-pot syntheses of glutaronitrile derivatives.