10150-27-3Relevant articles and documents
Valorization of furfural using ruthenium (II) complexes containing phosphorus-nitrogen ligands under homogeneous transfer hydrogen condition
Aguirre, Pedro,Aranda, Braulio,López, Vicente,Moya, Sergio A.,Parra-Melipán, Sebastián,Valdebenito, Gonzalo
, (2021)
In this paper, we report the catalytic activity of a series of ruthenium (II) complexes containing phosphorus-nitrogen bidentated (P-N) ligands in the hydrogenation of furfural via hydrogen transfer reaction using two hydrogen donor sources: 2-propanol in basic medium and formic acid under mild conditions. The results showed that all the ruthenium complexes studied are catalytically active in the hydrogenation of furfural by hydrogen transfer reaction; they showed 100% conversion with both hydrogen sources. However, selectivities towards the formation of furfuryl alcohol were better when formic acid was used. It was also found that the reaction studied in a basic medium competes with the Cannizzaro reaction, obtaining furfuryl alcohol and furoic acid in a 70/30 ratio; on the other hand, using formic acid as the hydrogen source yields furfuryl alcohol with 100% selectivity. Although formic acid can be used as a hydrogen source successfully. The optimal substrate/acid ratio was found to be 1:1, as a higher concentration of formic acid can cause catalyst decomposition. The yielded products, furfuryl alcohol and furoic acid, obtained from renewable sources, have multiple applications in the organic chemical industry, replacing or complementing similar fossil-derived products.
Catalytic hydrophosphination of styrenes
Shulyupin, Mstislav O.,Kazankova, Marina A.,Beletskaya, Irina P.
, p. 761 - 763 (2002)
(equation presented) The first example of intermolecular hydrophosphination of styrenes catalyzed by Ni and Pd complexes is described. The reaction of Ph2PH with styrene, 4-vinylpyridine, 2-vinylpyridine, 4-methoxystyrene, 2-methoxystyrene, and 5-vinyl-2-methylpyridine in benzene under Ni[P(OEt)3]4 catalysis proceeds with high yield and selectivity to give only anti-Markovnikov product.
t-BuOK-catalyzed addition phosphines to functionalized alkenes: A convenient synthesis of polyfunctional phosphine derivatives
Bunlaksananusorn, Tanasri,Knochel, Paul
, p. 5817 - 5819 (2002)
The use of t-BuOK in DMSO allows a smooth addition of Ph2PH, Cy2PH and Ph2P(O)H to various functionalized alkenes leading to polyfunctional phosphines in good yields. This method has been used to prepare precursors for P,P- and P,N-ligands.
Visible Light Photocatalysis Using a Commercially Available Iron Compound
Pagano, Justin K.,Bange, Christine A.,Farmiloe, Sarah E.,Waterman, Rory
, p. 3891 - 3895 (2017)
[CpFe(CO)2]2 (1) (Cp = η5-C5H5) is an effective precatalyst for the hydrophosphination of alkenes with Ph2PH under visible light irradiation, which appears to be a unique way to promote metal-catalyzed hydrophosphination. Additionally, 1 is a photocatalyst for the dehydrogenation of amine boranes and formation of siloxanes from tertiary silanes. These reactions have similar, if not improved, reactivity over the same transformations using 1 or related CpFeMe(CO)2 under UV irradiation, consistent with the notion that hydrophosphination with 1 proceeds via formation of CpFe(CO)2?. These results demonstrate that catalyst selection can avail the use of commercially available LED bulbs as photon sources, potentially replacing mercury arc lamps or other energy intensive processes in known or new catalytic reactions.
Neutral and Cationic Zirconium Complexes Bearing Multidentate Aminophenolato Ligands for Hydrophosphination Reactions of Alkenes and Heterocumulenes
Zhang, Yu,Qu, Liye,Wang, Yaorong,Yuan, Dan,Yao, Yingming,Shen, Qi
, p. 139 - 149 (2018/01/11)
Zirconium complexes supported by multidentate aminophenolato ligands were synthesized and characterized. The catalytic activities of neutral zirconium complexes and their cationic derivatives in the hydrophosphination of alkenes as well as heterocumulenes have been investigated and compared. Neutral complex 1 bearing a multidentate amino mono(phenolato) ligand exhibited high activity in hydrophosphination of simple alkenes, and anti-Markovnikov products were obtained in 37-94% yields at room temperature. Cationic species generated in situ from complex 3 stabilized by a bis(phenolato) ligand were found to be more active for hydrophosphination of heterocumulenes, i.e., carbodiimides and isocyanates, and gave phosphaguanidines and phosphaureas in 67-93% yields. The Lewis acidity and coordination space of metal centers are modified through changes in the ligand structure, which is found to significantly influence catalytic activity. These complexes are among the most active group 4 metal-based catalysts for hydrophosphination reactions.
