1354948-36-9Relevant academic research and scientific papers
Nickel-catalyzed alkylation and transfer hydrogenation of α,β-unsaturated enones with methanol
Castellanos-Blanco, Nahury,Flores-Alamo, Marcos,Garcia, Juventino J.
experimental part, p. 680 - 686 (2012/04/10)
Complexes of the type [{(dippe)Ni} ( 2-Cα,Cβ- 1,4-dien-3-one)] (dippe = 1,2-bis(diisopropylphosphino)- ethane); n= 1, 2; enone = aromatic 1,4-pentadien-3-ones) were synthesized. The "[(dippe)Ni]" moiety derived from [(dippe)Ni(-H)]2 2-coordinated to the C,C double bonds of the corresponding α,β-unsaturated enone and was fully characterized using a variety of spectroscopic techniques, for instance, single-crystal X-ray diffraction, nuclear magnetic resonance (NMR), and mass spectrometry. The complexes were assessed in a catalytic transfer hydrogenation process using methanol (CH3OH) as a hydrogen donor. This alcohol turned out to be a very efficient reducing and alkylating agent of 1,4- pentadien-3-ones, under neat conditions. The current methodology allowed the selective reduction of C=C bonds in α,β- unsaturated enones to yield enones and saturated ketones by a homogeneous catalytic pathway, whereas by a heterogeneous pathway, the process leads to the formation of mono- and dimethylated ketones. In the latter case, the occurrence of nickel nanoparticles in the reaction media was found to participate in the catalytic alkylation of such dienones.
