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A pentanuclear yttrium hydroxo cluster as an oxidation catalyst. Catalytic oxidation of aldehydes in the presence of air
The air- and moisture-stable pentanuclear yttrium cluster H 5[Y5(μ4-O)(μ3-O) 4(μ-η2-Ph2acac) 4(η2-Ph2acac)6] (Ph 2acac = dibenzoylmethanide) has been used as a homogenous catalyst for the oxidation of aldehydes to the corresponding carboxylic acids in the presence of air.
Roesky, Peter W.,Canseco-Melchor, Graciela,Zulys, Agustino
p. 738 - 739
(2004)
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Hydrogenation of Esters by Manganese Catalysts
The hydrogenation of esters catalyzed by a manganese complex of phosphine-aminopyridine ligand was developed. Using this protocol, a variety of (hetero)aromatic and aliphatic carboxylates including biomass-derived esters and lactones were hydrogenated to primary alcohols with 63–98% yields. The manganese catalyst was found to be active for the hydrogenation of methyl benzoate, providing benzyl alcohol with turnover numbers (TON) as high as 45,000. Investigation of catalyst intermediates indicated that the amido manganese complex was the active catalyst species for the reaction. (Figure presented.).
Li, Fu,Li, Xiao-Gen,Xiao, Li-Jun,Xie, Jian-Hua,Xu, Yue,Zhou, Qi-Lin
(2022/01/13)

Ambient-pressure highly active hydrogenation of ketones and aldehydes catalyzed by a metal-ligand bifunctional iridium catalyst under base-free conditions in water
A green, efficient, and high active catalytic system for the hydrogenation of ketones and aldehydes to produce corresponding alcohols under atmospheric-pressure H2 gas and ambient temperature conditions was developed by a water-soluble metal–ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(OH)][Na] in water without addition of a base. The catalyst exhibited high activity for the hydrogenation of ketones and aldehydes. Furthermore, it was worth noting that many readily reducible or labile functional groups in the same molecule, such as cyan, nitro, and ester groups, remained unchanged. Interestingly, the unsaturated aldehydes can be also selectively hydrogenated to give corresponding unsaturated alcohols with remaining C=C bond in good yields. In addition, this reaction could be extended to gram levels and has a large potential of wide application in future industrial.
Wang, Rongzhou,Yue, Yuancheng,Qi, Jipeng,Liu, Shiyuan,Song, Ao,Zhuo, Shuping,Xing, Ling-Bao
p. 1 - 7
(2021/05/17)

Method for synthesizing unsaturated primary alcohol in water phase
The invention discloses a method for synthesizing unsaturated primary alcohol in a water phase. The method comprises the following steps: taking unsaturated aldehyde as a raw material, selecting water as a solvent, and carrying out catalytic hydrogenation reaction on the unsaturated aldehyde in the presence of a water-soluble catalyst to obtain the unsaturated primary alcohol, wherein the catalyst is a metal iridium complex [Cp * Ir (2, 2'-bpyO)(OH)][Na]. Water is used as the solvent, so that the use of an organic solvent is avoided, and the method is more environment-friendly; the reaction is carried out at relatively low temperature and normal pressure, and the reaction conditions are mild; alkali is not needed in the reaction, so that generation of byproducts is avoided; and the conversion rate of the raw materials is high, and the yield of the obtained product is high. The method not only has academic research value, but also has a certain industrialization prospect.and.
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Paragraph 0037-0038

(2021/07/14)

Application of bis(phosphinite) pincer nickel complexes to the catalytic hydrosilylation of aldehydes
A series of bis(phosphinite) (POCOP) pincer ligated nickel complexes, [2,6-(tBu2PO)2C6H3]NiX (X = SH, 1; SCH2Ph, 2; SPh, 3; NCS, 4; N3, 5), were used to catalyse the hydrosilylation of aldehydes. It was found that both complexes 1 and 2 are active in catalysing the hydrosilylation of aldehydes with phenylsilane and complex 1 is comparatively more active. The expected alcohols were isolated in good to excellent yields after basic hydrolysis of the resultant hydrosilylation products. However, no reaction was observed when complex 3 or 4 or 5 was used as the catalyst. The results are consistent with complexes 1 and 2 serving as catalyst precursors, which generate the corresponding nickel hydride complex [2,6-(tBu2PO)2C6H3]NiH in situ, and the nickel hydride complex is the active species that catalyses this hydrosilylation process. The in situ generation of the nickel hydride species was supported by both experimental results and DFT calculation.
Chang, Jiarui,Fang, Fei,Tu, Chenhao,Zhang, Jie,Ma, Nana,Chen, Xuenian
(2020/10/27)

Efficient Solvent-Free Hydrosilylation of Aldehydes and Ketones Catalyzed by Fe2(CO)9/C6H4-o-(NCH2PPh2)2BH
An efficient solvent-free catalyst system for hydrosilylation of aldehydes and ketones was developed based on iron pre-catalyst Fe2(CO)9/C6H4-o-(NCH2PPh2)2BH. The reactions were tolerant of many functional groups and the corresponding alcohols were isolated in good to excellent yields following basic hydrolysis of the reaction products. The reaction is likely catalyzed by an in situ generated pincer ligated iron hydride complex. Graphic Abstract: [Figure not available: see fulltext.]
Fang, Fei,Chang, Jiarui,Zhang, Jie,Chen, Xuenian
p. 3509 - 3515
(2021/03/16)

A Water/Toluene Biphasic Medium Improves Yields and Deuterium Incorporation into Alcohols in the Transfer Hydrogenation of Aldehydes
Deuterium labeling is an interesting process that leads to compounds of use in different fields. We describe the transfer hydrogenation of aldehydes and the selective C1 deuteration of the obtained alcohols in D2O, as the only deuterium source. Different aromatic, alkylic and α,β-unsaturated aldehydes were reduced in the presence of [RuCl(p-cymene)(dmbpy)]BF4, (dmbpy=4,4′-dimethyl-2,2′-bipyridine) as the pre-catalyst and HCO2Na/HCO2H as the hydrogen source. Moreover, furfural and glucose, were selectively reduced to the valuable alcohols, furfuryl alcohol and sorbitol. The processes were carried out in neat water or in a biphasic water/toluene system. The biphasic system allowed easy recycling, higher yields, and higher selective D incorporation (using D2O/toluene). The deuteration took place due to an efficient effective M–H/D+ exchange from D2O that allows the inversion of polarity of D+ (umpolung). DFT calculations that explain the catalytic behavior in water are also included.
Ruiz-Casta?eda, Margarita,Santos, Lucía,Manzano, Blanca R.,Espino, Gustavo,Jalón, Félix A.
p. 1358 - 1372
(2021/03/16)

Sodium Aminodiboranate, a New Reagent for Chemoselective Reduction of Aldehydes and Ketones to Alcohols
Sodium aminodiboranate (NaNH 2(BH 3) 2, NaADBH) is a new member of the old borane family, which exhibits superior performance in chemoselective reduction. Experimental results show that NaADBH can rapidly reduce aldehydes and ketones to the corresponding alcohols in high efficiency and selectivity under mild conditions. There are little steric and electronic effects on this reduction.
Wang, Jin,Guo, Yu,Li, Shouhu,Chen, Xuenian
supporting information
p. 1104 - 1108
(2021/05/25)

Ruthenium-catalyzed ester reductions applied to pharmaceutical intermediates
Ruthenium pincer complexes were synthesized and used for catalytic ester reductions under mild conditions (～5 bar of hydrogen). An experimental design approach was used to optimize the conditions for yield, purity, and robustness. Evidence for the catalytically active ruthenium dihydride species is presented. Observed intermediates and side products, as well as time-course data, were used to build mechanistic insight. The optimized procedure was further demonstrated through scaled-up reductions of two pharmaceutically relevant esters, both in batch and continuous flow.
Shaalan, Youssef,Boulton, Lee,Jamieson, Craig
supporting information
p. 2745 - 2751
(2020/11/30)

Biomimetic Hydrogenation Catalyzed by a Manganese Model of [Fe]-Hydrogenase
[Fe]-hydrogenase is an efficient biological hydrogenation catalyst. Despite intense research, Fe complexes mimicking the active site of [Fe]-hydrogenase have not achieved turnovers in hydrogenation reactions. Herein, we describe the design and development of a manganese(I) mimic of [Fe]-hydrogenase. This complex exhibits the highest activity and broadest scope in catalytic hydrogenation among known mimics. Thanks to its biomimetic nature, the complex exhibits unique activity in the hydrogenation of compounds analogous to methenyl-H4MPT+, the natural substrate of [Fe]-hydrogenase. This activity enables asymmetric relay hydrogenation of benzoxazinones and benzoxazines, involving the hydrogenation of a chiral hydride transfer agent using our catalyst coupled to Lewis acid-catalyzed hydride transfer from this agent to the substrates.
Hu, Xile,Pan, Hui-Jie
supporting information
p. 4942 - 4946
(2020/02/11)

Hydrosilylation of Aldehydes and Ketones Catalysed by Bis(phosphinite) Pincer Platinum Hydride Complexes
Bis(phosphinite) pincer platinum hydride complexes, [2,6-(R2PO)2C6H3]PtH (R=tBu, iPr), were synthesized, characterized and applied to the hydrosilylation of aldehydes and ketones. NMR study and single crystal X-ray diffraction analysis indicated that the hydrides in these two platinum complexes are comparatively less hydridic: down-field 1H NMR resonances (0.71 and 0.98 ppm) and weak Pt?H interactions were observed. Both the platinum complexes were found to be good catalysts for the hydrosilylation of aldehydes and ketones with phenylsilane. The corresponding alcohols were isolated in good to excellent yields following basic hydrolysis of the resultant hydrosilylation products and turnover frequencies (TOFs) up to 3200 h?1 were achieved at 60 °C in toluene, which are much higher than those of the hydrosilylation catalysed by the corresponding nickel pincer hydride complexes. A possible mechanism for the present hydrosilylation process was discussed. (Figure presented.).
Chang, Jiarui,Fang, Fei,Zhang, Jie,Chen, Xuenian
p. 2709 - 2715
(2020/06/02)

Novel clamp metal complex and application thereof
The invention discloses a method for preparing a novel clamp-shaped complex and application of the novel clamp-shaped complex in the reaction of catalytic hydrogenation of carboxylic acid ester compounds to produce corresponding alcohols and reaction of carbon dioxide catalytic hydrogenation to form formamide compounds. Carboxylic acid esters and hydrogen as raw materials or carbon dioxide, hydrogen and amine compounds as raw materials are reacted in an organic solvent condition or a solvent-free condition in the presence of a transition metal complex as a catalyst to respectively form the corresponding alcohol compounds and/or corresponding formamide compounds. The method has the advantages of being high in reaction efficiency, good in selectivity, mild in conditions, economical, environmentally-friendly, and simple in operation, and has good promotion and application prospects.
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Paragraph 0410-0412; 0446-0449; 0515-0518

(2019/04/26)

General and Phosphine-Free Cobalt-Catalyzed Hydrogenation of Esters to Alcohols
Catalytic hydrogenation of esters is essential for the sustainable production of alcohols in organic synthesis and chemical industry. Herein, we describe the first non-noble metal catalytic system that enables an efficient hydrogenation of non-activated esters to alcohols in the absence of phosphine ligands (with a maximum turnover number of 2391). The general applicability of this protocol was demonstrated by the high-yielding hydrogenation of 39 ester substrates including aromatic/aliphatic esters, lactones, polyesters and various pharmaceutical molecules.
Shao, Zhihui,Zhong, Rui,Ferraccioli, Raffaella,Li, Yibiao,Liu, Qiang
supporting information
p. 1125 - 1130
(2019/10/22)

Dehydroalkylative Activation of CNN- A nd PNN-Pincer Ruthenium Catalysts for Ester Hydrogenation
Ruthenium-pincer complexes bearing CNN- A nd PNN-pincer ligands with diethyl-or diisopropylamino side groups, which have previously been reported to be active precatalysts for ester hydrogenation, undergo dehydroalkylation on heating in the presence of tricyclohexylphosphine to release ethane or propane, giving five-coordinate ruthenium(0) complexes containing a nascent imine functional group. Ethane or propane is also released under the conditions of catalytic ester hydrogenation, and time-course studies show that this release is concomitant with the onset of catalysis. A new PNN-pincer ruthenium(0)-imine complex is a highly active catalyst for ester hydrogenation at room temperature, giving up to 15500 turnovers with no added base. This complex was shown to react reversibly at room temperature with two equivalents of hydrogen to give a ruthenium(II)-dihydride complex, where the imine functionality has been hydrogenated to give a protic amine side group. These observations have potentially broad implications for the identities of catalytic intermediates in ester hydrogenation and related transformations.
He, Tianyi,Buttner, John C.,Reynolds, Eamon F.,Pham, John,Malek, Jack C.,Keith, Jason M.,Chianese, Anthony R.
supporting information
p. 17404 - 17413
(2019/11/03)

Diaminodiphosphine tetradentate ligand and ruthenium complex thereof, and preparation methods and applications of ligand and complex
The invention discloses a diaminodiphosphine tetradentate ligand and a ruthenium complex thereof, and preparation methods and applications of the ligand and the complex, and provides a ruthenium complex represented by a formula I, wherein L is a diaminodiphosphine tetradentate ligand represented by a formula II, and X and Y are respectively and independently chlorine ion, bromine ion, iodine ion,hydrogen negative ion or BH4. According to the present invention, the ruthenium complex exhibits excellent catalytic activity in the catalytic hydrogenation reactions of ester compounds, has high yield and high chemical selectivity, is compatible with conjugated and non-conjugated carbon-carbon double bond, carbon-carbon triple bond, epoxy, halogen, carbonyl and other functional groups, and hasgreat application prospects.
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Paragraph 0307-0309; 0311

(2019/11/04)

Method for synthesizing unsaturated primary alcohol
The invention discloses a method for synthesizing an unsaturated primary alcohol. The method comprises the following steps: adding an unsaturated aldehyde, a transition metal catalyst iridium complexand isopropyl alcohol in a reaction container, heating the reaction mixture in an oil bath, carrying out a reaction for a plurality of hours, then carrying out cooling to room temperature, removing the solvent by rotating evaporation, and then carrying out column separation to obtain the target compound. According to the invention, the unsaturated aldehyde is used as a raw material, isopropyl alcohol is used as a hydrogen source and the solvent, and the unsaturated primary alcohol is generated through hydrogen transfer under participation of the transition metal iridium catalyst. The method has the following remarkable advantages: 1) the reaction temperature is low; 2) cheap, safe and non-toxic isopropanol is used; 3) the catalyst usage amount is low, and reaction atom economy is high; and4) selectivity is good. Therefore, the method meets the requirements of green chemistry and has a wide development prospect.
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Paragraph 0084-0088

(2019/08/20)

Ambient-pressure hydrogenation of ketones and aldehydes by a metal-ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(H2O)] without using base
An efficient catalytic system for hydrogenation of ketones and aldehydes using a Cp*Ir complex [Cp*Ir(2,2′-bpyO)(H2O)] bearing a bipyridine-based functional ligand as catalyst has been developed. A wide variety of secondary and primary alcohols were synthesized by the catalyzed hydrogenation of ketones and aldehydes under facile atmospheric-pressure without a base. The catalyst also displays an excellent chemoselectivity towards other carbonyl functionalities and unsaturated motifs. This catalytic system exhibits high activity for hydrogenation of ketones and aldehydes with H2 gas.
Wang, Rongzhou,Qi, Jipeng,Yue, Yuancheng,Lian, Zhe,Xiao, Haibin,Zhuo, Shuping,Xing, Lingbao
(2019/07/30)

Synthesis, characterization and catalytic activity of novel ruthenium complexes bearing NNN click based ligands
Novel air stable ruthenium(ii) complexes bearing tridentate ligands bis((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine (L1), 1-(1-benzyl-1H-1,2,3-triazol-4-yl)-N-(pyridin-2-ylmethyl)methanamine (L2) or 2-(4-phenyl-1H-1,2,3-triazol-1-yl)-N-(pyridin-2-ylmethyl)ethan-1-amine (L3) were synthesised. The nitrogen based ligands were easily prepared by virtue of click chemistry using cheap and commercially available reagents. The ruthenium complexes were obtained by heating the Ru(PPh3)3Cl2 precursor and the tridentate NNN ligand in toluene under reflux for 2 hours, achieving yields of 82-87%. These complexes were fully characterized by means of NMR, FT-IR and high resolution ESI spectroscopy. The crystal structure of one of the complexes was determined. These complexes showed excellent activity and selectivity in the hydrogenation of ketones and aldehydes. DFT calculations show that complex 3 may react through an outer-sphere catalytic cycle rather than via an inner-sphere mechanism.
Sole, Roberto,Bortoluzzi, Marco,Spannenberg, Anke,Tin, Sergey,Beghetto, Valentina,De Vries, Johannes G.
p. 13580 - 13588
(2019/09/30)

Chemoselective transfer hydrogenation of aldehydes in aqueous media catalyzed by a well-defined iron(II) hydride complex
Abstract: An iron(II) hydride PNP pincer complex is applied as catalyst for the chemoselective transfer hydrogenation of aldehydes using an aqueous solution of sodium formate as hydrogen source. A variety of aromatic, heteroaromatic, and aliphatic aldehydes could be reduced to the corresponding alcohols in good to excellent yields with a catalyst loading of 1.0?mol% at 80?°C and 1?h reaction time. If present, C–C double bonds remained unaffected in course of the reaction, even when they are conjugated to the carbonyl group of the aldehyde. The catalyst’s lifetime and activity could be improved when the reactions were conducted in an ionic liquid-based micro emulsion. Graphical abstract: [Figure not available: see fulltext.].
Gorgas, Nikolaus,Ilic, Aleksandra,Kirchner, Karl
p. 121 - 126
(2018/11/01)

Tris(pyrazolyl)borate Cobalt-Catalyzed Hydrogenation of C=O, C=C, and C=N Bonds: An Assistant Role of a Lewis Base
The combination of tris(pyrazolyl)borate cobalt complexes and Lewis base is developed as an efficient catalyst precursor in the homogeneous hydrogenation. A broad substrate scope including carbonyls, alkenes, enamines, and imines is reduced with 60 atm of H2 at 60 °C. Mechanistic studies support the hydrogenation operates through a frustrated Lewis pair (FLP)-like reduction process. These results highlight the development of novel non-noble metal catalytic processes, when combined with the diverse small molecule activation chemistry associated with FLPs.
Lin, Yang,Zhu, De-Ping,Du, Yi-Ran,Zhang, Rui,Zhang, Suo-Jiang,Xu, Bao-Hua
supporting information
p. 2693 - 2698
(2019/04/25)

Influence of the Ionic Liquid on the Activity of a Supported Ionic Liquid Phase FeII Pincer Catalyst for the Hydrogenation of Aldehydes
The catalytic hydrogenation of different aldehydes to the corresponding alcohols was investigated using an FeII hydride pincer complex as catalyst in the supported ionic liquid phase (SILP) reaction mode. Two different ionic liquids of the type [X4441][NTf2] with X=N or P were applied with mesoporous silica gel as support, which was coated first with a chemisorbed monolayer of the corresponding modified IL to remove acidic surface OH-groups and to prevent IL leaching. Quantitative conversion with turn-over frequencies in the order of 1000 h– 1 were obtained for various aromatic and heteroaromatic aldehydes and highly selective aldehyde reduction was observed also for substrates containing reducible C=C bonds. Aldehydes with longer aliphatic chains or cycloalkyl substituents, however, showed no conversion here, in contrast to a previous study with an imidazolium-based ionic liquid. These differences were ascribed primarily to differences in substrate/ionic liquid interactions. Whereas [N4441][NTf2] and [P4441][NTf2] gave essentially identical results for different substrates in single-batch reactions, prolonged use of the catalyst in repeated reaction cycles lead to a quick drop-off in catalyst activity in [P4441][NTf2], but a continuous, quantitative conversion in [N4441][NTf2].
Csendes, Zita,Brünig, Julian,Yigit, Nevzat,Rupprechter, Günther,Bica-Schr?der, Katharina,Hoffmann, Helmuth,Kirchner, Karl
p. 3503 - 3510
(2019/08/12)

Inexpensive Ruthenium NNS-Complexes as Efficient Ester Hydrogenation Catalysts with High C=O vs. C=C Selectivities
Ru(NNS)(PPh3)Cl2 (NNS=2-(methylthio)-N-(pyridin-2-yl-methyl)ethan-1-amine) was employed in the hydrogenation of α,β-unsaturated esters, reaching selectivities for the allylic alcohol up to 95% in the hydrogenation of iso-butylcinnamate. In addition, several ester substrates were hydrogenated with catalyst loadings as low as 0.05?mol%. Surprisingly, selectivity of the hydrogenation of the C=O vs the C=C bonds strongly depends on the solvent. (Figure presented.).
Stadler, Bernhard M.,Puylaert, Pim,Diekamp, Justus,van Heck, Richard,Fan, Yuting,Spannenberg, Anke,Hinze, Sandra,de Vries, Johannes G.
supporting information
p. 1151 - 1158
(2018/02/06)

A Selective and Functional Group-Tolerant Ruthenium-Catalyzed Olefin Metathesis/Transfer Hydrogenation Tandem Sequence Using Formic Acid as Hydrogen Source
A ruthenium-catalyzed transfer hydrogenation of olefins utilizing formic acid as a hydrogen donor is described. The application of commercially available alkylidene ruthenium complexes opens access to attractive C(sp3)-C(sp3) bond formation in an olefin metathesis/transfer hydrogenation sequence under tandem catalysis conditions. High chemoselectivity of the developed methodology provides a remarkable synthetic tool for the reduction of various functionalized alkenes under mild reaction conditions. The developed methodology is applied for the formal synthesis of the drugs pentoxyverine and bencyclane.
Zieliński, Grzegorz K.,Majtczak, Jaros?awa,Gutowski, Maciej,Grela, Karol
p. 2542 - 2553
(2018/03/09)

Cobalt Pincer Complexes for Catalytic Reduction of Carboxylic Acid Esters
A selection of cobalt(I) and cobalt(II) pincer type complexes with different substitution patterns was tested in the catalytic reduction of carboxylic acid esters to alcohols. The cobalt pincer type complex 4 is suitable for the hydrogenation of aromatic as well as aliphatic and cyclic esters. Mechanistic investigation indicated a metal ligand cooperated reaction pathway.
Junge, Kathrin,Wendt, Bianca,Cingolani, Andrea,Spannenberg, Anke,Wei, Zhihong,Jiao, Haijun,Beller, Matthias
supporting information
p. 1046 - 1052
(2018/01/01)

Highly efficient hydroboration of carbonyl compounds catalyzed by tris(methylcyclopentadienyl)lanthanide complexes
Homoleptic lanthanide complexes coordinated by a Me-substituted Cp ligand [(MeCp)3Ln] demonstrate unprecedentedly high efficiency in catalyzing the hydroboration of aldehydes and ketones with pinacolborane. This protocol is also applicable for the hydroboration of aryl-substituted imines. In addition, broad functional group compatibility and excellent chemoselectivity is also achieved. DFT calculations are employed to shed light on the reaction mechanism.
Yan, Dandan,Dai, Ping,Chen, Sufang,Xue, Mingqiang,Yao, Yingming,Shen, Qi,Bao, Xiaoguang
p. 2787 - 2791
(2018/04/27)

Transfer Hydrogenation of Aldehydes and Ketones with Isopropanol under Neutral Conditions Catalyzed by a Metal-Ligand Bifunctional Catalyst [Cp?Ir(2,2′-bpyO)(H2O)]
A Cp?Ir complex bearing a functional bipyridonate ligand [Cp?Ir(2,2′-bpyO)(H2O)] was found to be a highly efficient and general catalyst for transfer hydrogenation of aldehydes and chemoselective transfer hydrogenation of unsaturated aldehydes with isopropanol under neutral conditions. It was noteworthy that many readily reducible or labile functional groups such as nitro, cyano, ester, and halide did not undergo any change under the reaction conditions. Furthermore, this catalytic system exhibited high activity for transfer hydrogenation of ketones with isopropanol. Notably, this research exhibited new potential of metal-ligand bifunctional catalysts for transfer hydrogenation.
Wang, Rongzhou,Tang, Yawen,Xu, Meng,Meng, Chong,Li, Feng
p. 2274 - 2281
(2018/02/23)

Carbonyl and ester C-O bond hydrosilylation using κ4-diimine nickel catalysts
The synthesis of alkylphosphine-substituted α-diimine (DI) ligands and their subsequent addition to Ni(COD)2 allowed for the preparation of (iPr2PPrDI)Ni and (tBu2PPrDI)Ni. The solid state structures of both compounds were found to feature a distorted tetrahedral geometry that is largely consistent with the reported structure of the diphenylphosphine-substituted variant, (Ph2PPr DI)Ni. To explore and optimize the synthetic utility of this catalyst class, all three compounds were screened for benzaldehyde hydrosilylation activity at 1.0 mol% loading over 3 h at 25 °C. Notably, (Ph2PPr DI)Ni was found to be the most efficient catalyst while phenyl silane was the most effective reductant. A broad scope of aldehydes and ketones were then hydrosilylated, and the silyl ether products were hydrolyzed to afford alcohols in good yield. When attempts were made to explore ester reduction, inefficient dihydrosilylation was noted for ethyl acetate and no reaction was observed for several additional substrates. However, when an equimolar solution of allyl acetate and phenyl silane was added to 1.0 mol% (Ph2PPr DI)Ni, complete ester C-O bond hydrosilylation was observed within 30 min at 25 °C to generate propylene and PhSi(OAc)3. The scope of this reaction was expanded to include six additional allyl esters, and under neat conditions, turnover frequencies of up to 990 h-1 were achieved. This activity is believed to be the highest reported for transition metal-catalyzed ester C-O bond hydrosilylation. Proposed mechanisms for (Ph2PPr DI)Ni-mediated carbonyl and allyl ester C-O bond hydrosilylation are also discussed.
Rock, Christopher L.,Groy, Thomas L.,Trovitch, Ryan J.
supporting information
p. 8807 - 8816
(2018/07/13)

Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates
Ligand-enabled aza-Heck cyclizations and cascades of N-(pentafluorobenzoyloxy)carbamates are described. These studies encompass the first examples of efficient non-biased 6-exo aza-Heck cyclizations. The methodology provides direct and flexible access to carbamate protected pyrrolidines and piperidines.
Hazelden, Ian R.,Carmona, Rafaela C.,Langer, Thomas,Pringle, Paul G.,Bower, John F.
supporting information
p. 5124 - 5128
(2018/03/26)

Selective Hydrogenation of Aldehydes Using a Well-Defined Fe(II) PNP Pincer Complex in Biphasic Medium
A biphasic process for the hydrogenation of aldehydes was developed using a well-defined iron (II) PNP pincer complex as model system to investigate the performance of various ionic liquids. A number of suitable hydrophobic ionic liquids based on the N(Tf)2? anion were identified, allowing to immobilize the iron (II) catalyst in the ionic liquid layer and to facilitate the separation of the desired alcohols. Further studies showed that targeted Br?nsted basic ionic liquids can eliminate the need of an external base to activate the catalyst.
Weber, Stefan,Brünig, Julian,Zeindlhofer, Veronika,Schr?der, Christian,St?ger, Berthold,Limbeck, Andreas,Kirchner, Karl,Bica, Katharina
p. 4386 - 4394
(2018/09/14)

Chemoselective Supported Ionic-Liquid-Phase (SILP) Aldehyde Hydrogenation Catalyzed by an Fe(II) PNP Pincer Complex
A base-tolerant supported ionic-liquid-phase (SILP) system containing a well-defined hydride Fe(II) PNP pincer complex has been prepared, structurally characterized, and used as catalyst in the hydrogenation of aldehydes to alcohols. The new SILP catalyst, with the optimum pore filling, was highly active exhibiting TONs and TOFs of up to 1000 and 4000 h-1, respectively, under mild conditions (25 °C, 10-50 bar H2 pressure) without significant leaching of both the complex and the IL.
Brünig, Julian,Csendes, Zita,Weber, Stefan,Gorgas, Nikolaus,Bittner, Roland W.,Limbeck, Andreas,Bica, Katharina,Hoffmann, Helmuth,Kirchner, Karl
p. 1048 - 1051
(2018/02/14)

Porous, Naturally Derived Hafnium Phytate for the Highly Chemoselective Transfer Hydrogenation of Aldehydes with Other Reducible Moieties
Both the utilization of naturally occurring compounds to prepare functional materials and the selective conversion of aldehydes with other reducible moieties (ORMs) are very attractive topics. Herein, we synthesized a novel porous material, hafnium phytate (Hf-Phy), by using naturally derived sodium phytate as the building block. Hf-Phy has plenty of mesopores centered around 11.8 nm. Hf-Phy showed excellent performance for the transfer hydrogenation of aldehydes with ORMs by using 2-propanol as the hydrogen source with high selectivities (95–100 %) for alcohols without reducing ORMs. Systematic studies suggested that the oxophilicity of Hf4+ and the basicity and structure of Hf-Phy contributed significantly to the excellent performance. Additionally, Hf-Phy could be used over at least five cycles without any decrease in activity or selectivity.
Song, Jinliang,Xue, Zhimin,Xie, Chao,Wu, Haoran,Liu, Shuaishuai,Zhang, Lujun,Han, Buxing
p. 725 - 730
(2018/01/22)

Chemoselective Hydrogenation of Aldehydes under Mild, Base-Free Conditions: Manganese Outperforms Rhenium
Several hydride Mn(I) and Re(I) PNP pincer complexes were applied as catalysts for the homogeneous chemoselective hydrogenation of aldehydes. Among these, [Mn(PNP-iPr)(CO)2(H)] was found to be one of the most efficient base metal catalysts for this process and represents a rare example which permits the selective hydrogenation of aldehydes in the presence of ketones and other reducible functionalities, such as C=C double bonds, esters, or nitriles. The reaction proceeds at room temperature under base-free conditions with catalyst loadings between 0.1 and 0.05 mol% and a hydrogen pressure of 50 bar (reaching TONs of up to 2000). A mechanism which involves an outer-sphere hydride transfer and reversible PNP ligand deprotonation/protonation is proposed. Analogous isoelectronic and isostructural Re(I) complexes were only poorly active.
Glatz, Mathias,St?ger, Berthold,Himmelbauer, Daniel,Veiros, Luis F.,Kirchner, Karl
p. 4009 - 4016
(2018/05/23)

Chemoselective transfer hydrogenation of nitroarenes, ketones and aldehydes using acylthiourea based Ru(II)(p-cymene) complexes as precatalysts
A new series of Ru(II)(η6-p-cymene) complexes (1–5) was synthesized from pyridine based acylthiourea ligands (L1-L5) and [Ru(η6-p-cymene)Cl2]2. All the ligands and complexes were well characterized by UV-Visible, FT-IR, mass and 1H & 13C NMR spectroscopic techniques. The molecular structures of the ligands (L1, L2, L4 and L5) and complex 1 were confirmed using single crystal X-ray diffraction study. The Ru(II)(η6-p-cymene) complexes (1–5) were proved to be efficient precatalysts for the transfer hydrogenation of carbonyl compounds and nitroarenes in the presence of 2-propanol as a hydrogen donor and KOH as a base. The catalytic transfer hydrogenation reactions were chemoselective towards the nitro group in presence of carbonyl group, which is a rare scenario in homogeneous catalysis. The catalyst was compatible with broad range of substrates which include furfural, quinone and many heterocycles. The catalytic reactions exhibited very high conversions (upto 100%) and excellent yields (upto 99%). Turn Over Number (TON) was found upto 990.
Sathishkumar, Pushpanathan N.,Raveendran, Neethi,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
p. 57 - 65
(2018/10/05)

Gold-Catalyzed Stereoselective Synthesis of Bicyclic Lactams and Ketones from N-Tosylynamidomethyl-Tethered Cyclohexenes
Six-membered ring 3-enynamides underwent cycloisomerization in the presence of a catalytic amount of a gold(I) complex delivering mainly 4-azatricyclo[4.3.1.03,10]dec-2-ene derivatives and dibenz[cd,f]indole derivatives as the minor products under mild reaction conditions. Upon exposure to air, most aryl-substituted azatricycles led to bicyclic γ-lactams, while the ortho-tolyl- or alkyl-substituted azatricycles provided the corresponding bicyclic γ-lactams after oxidation with osmium tetraoxide and N-methylmorpholine-N-oxide. Under acidic conditions, the ortho-tolyl- or alkyl-substituted azatricycles were further transformed into 5-N-tosylaminomethyl-tethered bicyclo[4.2.0]octan-7-ones. The gold(I)-catalyzed tandem cycloisomerization/oxidation reaction also provided a new route for the synthesis of bridged bicyclic δ-lactams from six-membered ring 4-enynamides. The mild reaction conditions allowed the synthesis of a range of bicyclic γ- and δ-lactams and N-tosylaminomethyl-tethered bicyclo[4.2.0]octan-7-ones with high diastereoselectivities.
Zhong, Chang-Zhi,Tung, Po-Ting,Chao, Tsung-Han,Yeh, Ming-Chang P.
p. 481 - 501
(2017/04/26)

Mechanistic Investigation of Bis(imino)pyridine Manganese Catalyzed Carbonyl and Carboxylate Hydrosilylation
We recently reported a bis(imino)pyridine (or pyridine diimine, PDI) manganese precatalyst, (Ph2PPrPDI)Mn (1), that is active for the hydrosilylation of ketones and dihydrosilylation of esters. In this contribution, we reveal an expanded scope for 1-mediated hydrosilylation and propose two different mechanisms through which catalysis is achieved. Aldehyde hydrosilylation turnover frequencies (TOFs) of up to 4900 min-1 have been realized, the highest reported for first row metal-catalyzed carbonyl hydrosilylation. Additionally, 1 has been shown to mediate formate dihydrosilylation with leading TOFs of up to 330 min-1. Under stoichiometric and catalytic conditions, addition of PhSiH3 to (Ph2PPrPDI)Mn was found to result in partial conversion to a new diamagnetic hydride compound. Independent preparation of (Ph2PPrPDI)MnH (2) was achieved upon adding NaEt3BH to (Ph2PPrPDI)MnCl2 and single-crystal X-ray diffraction analysis revealed this complex to possess a capped trigonal bipyramidal solid-state geometry. When 2,2,2-trifluoroacetophenone was added to 1, radical transfer yielded (Ph2PPrPDI·)Mn(OC·(Ph)(CF3)) (3), which undergoes intermolecular C-C bond formation to produce the respective Mn(II) dimer, [(μ-O,Npy-4-OC(CF3)(Ph)-4-H-Ph2PPrPDI)Mn]2 (4). Upon finding 3 to be inefficient and 4 to be inactive, kinetic trials were conducted to elucidate the mechanisms of 1- and 2-mediated hydrosilylation. Varying the concentration of 1, substrate, and PhSiH3 revealed a first order dependence on each reagent. Furthermore, a kinetic isotope effect (KIE) of 2.2 ± 0.1 was observed for 1-catalyzed hydrosilylation of diisopropyl ketone, while a KIE of 4.2 ± 0.6 was determined using 2, suggesting 1 and 2 operate through different mechanisms. Although kinetic trials reveal 1 to be the more active precatalyst for carbonyl hydrosilylation, a concurrent 2-mediated pathway is more efficient for carboxylate hydrosilylation. Considering these observations, 1-catalyzed hydrosilylation is believed to proceed through a modified Ojima mechanism, while 2-mediated hydrosilylation occurs via insertion.
Mukhopadhyay, Tufan K.,Rock, Christopher L.,Hong, Mannkyu,Ashley, Daniel C.,Groy, Thomas L.,Baik, Mu-Hyun,Trovitch, Ryan J.
p. 4901 - 4915
(2017/04/11)

Zinc-Mediated Efficient and Selective Reduction of Carbonyl Compounds
We herein describe for the first time that an optimized combination of Zn and NH4Cl can be used for the selective reduction of aldehydes and ketones to the corresponding alcohols. The aldehyde and keto groups are selectively reduced in the presence of azide, cyano, epoxy, ester, and carbon–carbon double-bond functional groups. A broad functional-group compatibility, chemoselective reduction of aldehydes in the presence of ketones, and selective reduction of isatins at the C3 carbonyl group are the highlights of the present method.
Mandal, Tirtha,Jana, Snehasish,Dash, Jyotirmayee
p. 4972 - 4983
(2017/09/13)

Selective hydrogenation of unsaturated carbonyls by Ni-Fe-based alloy catalysts
Ni-Fe alloy catalysts prepared by a simple hydrothermal method and subsequent H2 treatment exhibited the greatest activity and selectivity for the hydrogenation of biomass-derived furfural to furfuryl alcohol among the examined second metals, such as Al, Ga, In, Co, and Ti. This work reveals that the alloying of Ni and Fe is a key factor in achieving highly selective hydrogenation of the CO moiety in unsaturated carbonyl substrates. We found that decreasing the temperature of H2 treatment (i.e. decreasing the crystallite size), e.g. Ni-Fe(2)HT-573 K (TOF = 952 h-1), increased the activity compared to that over Ni-Fe(2)HT-673 (TOF = 375 h-1) for furfural hydrogenation. This result suggests that a low-coordinated Ni-Fe alloy was imperative for the catalytic cycle. Moreover, the effect of the metal/support interface was critical; despite the high catalytic performance of Ni-Fe/TiO2, Ni-Fe/Al2O3, and Ni-Fe/CeO2, Ni-Fe supported on SiO2, taeniolite, and hydrotalcite catalysts were ineffective. Vibrational studies using FT-IR measurement confirmed that furfural was physically adsorbed on the surface of the Ni-Fe alloy catalyst via an η1(O) configuration. The synthetic scope of the Ni-Fe catalytic system was very broad; various types of unsaturated carbonyls, such as unsaturated aromatics, unconjugated aliphatics, and a large substituent, were selectively converted into the corresponding unsaturated alcohols.
Putro, Wahyu S.,Kojima, Takashi,Hara, Takayoshi,Ichikuni, Nobuyuki,Shimazu, Shogo
p. 3637 - 3646
(2017/08/21)

Syntheses, characterisation, and catalytic role of (η5-C5Me5)Rh(III) guanidinato complexes in transfer hydrogenation (TH) and TH-etherification
A family of air stable half sandwich meal guanidinato complexes ([(η5-Cp?)MCl{κ2(N,N′)((ArN)2C-N(H)Ar)}]) (M = Rh and Ir; Cp? = C5Me5; Ar = aryl) were synthesized in good yield and characterised by elemental analyses, IR, and NMR (1H, 13C, and 19F) spectroscopy. The geometry of the metal and the conformations of the guanidinate ligands in the complexes were studied by single crystal X-ray diffraction. The solution behaviour of representative complexes was investigated by detailed NMR studies including variable temperature and variable concentration 1H NMR measurements. The new complexes were screened as catalysts for transfer hydrogenation (TH) of acetophenone under basic and base free conditions and from these experiments, ([(η5-Cp?)RhCl{κ2(N,N′)((ArN)2C-N(H)Ar)}]) (Ar = 3,5-(CF3)2C6H3; 3) was chosen as the preferred catalyst due to its slightly better catalytic activity than other complexes. The utility of 3 in TH of a variety of carbonyl compounds was explored under basic and base free conditions. Tandem catalysis involving TH of a carbonyl group and etherification of the resulting -CH2OH group in reduction products of salicylaldehyde, 2-hydroxy-1-naphthaldehyde and 5-(hydroxymethyl)furfural was achieved in the presence of 3 under base free conditions. The role of the guanidinate ligands in the complexes for basic and base free TH of carbonyl compounds and TH-etherification tandem catalysis is discussed. Plausible mechanisms for TH and TH-etherification are outlined.
Kumar, Robin,Thirupathi, Natesan
p. 33890 - 33904
(2017/07/17)

Efficient carbon-supported heterogeneous molybdenum-dioxo catalyst for chemoselective reductive carbonyl coupling
Reductive coupling of various carbonyl compounds to the corresponding symmetric ethers with dimethylphenylsilane is reported using a carbon-supported dioxo-molybdenum catalyst. The catalyst is air- and moisture-stable and can be easily separated from the reaction mixture for recycling. In addition, the catalyst is chemoselective, thus enabling the synthesis of functionalized ethers without requiring sacrificial ligands or protecting groups.
Liu, Shengsi,Li, Jiaqi,Jurca, Titel,Stair, Peter C.,Lohr, Tracy L.,Marks, Tobin J.
p. 2165 - 2169
(2017/07/22)

Improved Second Generation Iron Pincer Complexes for Effective Ester Hydrogenation
Hydrogenation of esters to alcohols with a well-defined iron iPr2PNP pincer complex has been recently reported by us and other groups. We now introduce a novel and sterically less hindered Et2PNP congener that provides superior catalytic activity in the hydrogenation of various carboxylic acid esters and lactones compared to the known complex. Successful hydrogenation proceeds under relatively mild conditions (60°C) with lower catalyst loadings.
Elangovan, Saravanakumar,Wendt, Bianca,Topf, Christoph,Bachmann, Stephan,Scalone, Michelangelo,Spannenberg, Anke,Jiao, Haijun,Baumann, Wolfgang,Junge, Kathrin,Beller, Matthias
supporting information
p. 820 - 825
(2016/03/09)

Hydrogenation of Esters to Alcohols Catalyzed by Defined Manganese Pincer Complexes
The first manganese-catalyzed hydrogenation of esters to alcohols has been developed. The combination of Mn(CO)5Br with [HN(CH2CH2P(Et)2)2] leads to a mixture of cationic and neutral Mn PNP pincer complexes, which enable the reduction of various ester substrates, including aromatic and aliphatic esters as well as diesters and lactones. Notably, related pincer complexes with isopropyl or cyclohexyl substituents showed very low activity.
Elangovan, Saravanakumar,Garbe, Marcel,Jiao, Haijun,Spannenberg, Anke,Junge, Kathrin,Beller, Matthias
supporting information
p. 15364 - 15368
(2016/12/03)

Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts
Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo- and regioselectivity. Herein, we report a convenient one-pot process for this transformation that involves the unprecedented N-preferential group transfer of N-oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.
Nagasawa, Shota,Sasano, Yusuke,Iwabuchi, Yoshiharu
supporting information
p. 13189 - 13194
(2016/10/30)

Chelating Bis(1,2,3-triazol-5-ylidene) Rhodium Complexes: Versatile Catalysts for Hydrosilylation Reactions
NHC-rhodium complexes (NHC=N-heterocyclic carbenes) have been widely used as efficient catalysts for hydrosilylation reactions. However, the substrates were mostly limited to reactive carbonyl compounds (aldehydes and ketones) or carbon-carbon multiple bonds. Here, we describe the application of newly-developed chelating bis(tzNHC)-rhodium complexes (tz=1,2,3-triazol-5-ylidene) for several reductive transformations. With these catalysts, the formal reductive methylation of amines using carbon dioxide, the hydrosilylation of amides and carboxylic acids, and the reductive alkylation of amines using carboxylic acids have been achieved under mild reaction conditions.
Nguyen, Thanh V. Q.,Yoo, Woo-Jin,Kobayashi, Shu
supporting information
p. 452 - 458
(2016/02/12)

Synthesis of morphan derivatives with additional substituents in 8-position
The morphan system (2-azabicyclo[3.3.1]nonane) as a substructure of morphine is of major interest in medicinal chemistry. Herein, the synthesis of morphan derivatives with additional substituents at the propano bridge is reported. In order to avoid the isolation of the smelly and volatile nitrile 6 and the very polar primary amine 9, an efficient one-pot, three-step sequential transformation of the mesylate 5 into amides 10 was developed. The key step of the synthesis was the stereoselective intramolecular opening of the epoxides 11a-d leading to the exo-configured 8-hydroxymorphans 12a-d. The configuration of the exo-configured hydroxymorphan 12d bearing the ?- and s-pharmacophoric 3,4-dichlorophenylacetyl moiety was inverted by oxidation and stereoselective reduction. An X-ray crystal structure analysis of the benzamide 12c confirmed the relative configuration of the hydroxymorphans 12a-d and 14d.
Stefaowitz, Janine,Schepmann, Dirk,Daniliuc, Constantin,Saito, Susumu,Wünsch, Bernhard
p. 1057 - 1069
(2016/11/16)

Diverse N-Heterocyclic Ring Systems via Aza-Heck Cyclizations of N-(Pentafluorobenzoyloxy)sulfonamides
Aza-Heck cyclizations initiated by oxidative addition of Pd0-catalysts into the N?O bond of N-(pentafluoro-benzoyloxy)sulfonamides are described. These studies, which encompass only the second class of aza-Heck reaction developed to date, provide direct access to diverse N-heterocyclic ring systems.
Hazelden, Ian R.,Ma, Xiaofeng,Langer, Thomas,Bower, John F.
supporting information
p. 11198 - 11202
(2016/10/13)

Highly Efficient and Selective Hydrogenation of Aldehydes: A Well-Defined Fe(II) Catalyst Exhibits Noble-Metal Activity
The synthesis and application of [Fe(PNPMe-iPr)(CO)(H)(Br)] and [Fe(PNPMe-iPr)(H)2(CO)] as catalysts for the homogeneous hydrogenation of aldehydes is described. These systems were found to be among the most efficient catalysts for this process reported to date and constitute rare examples of a catalytic process which allows selective reduction of aldehydes in the presence of ketones and other reducible functionalities. In some cases, TONs and TOFs of up to 80000 and 20000 h-1, respectively, were reached. On the basis of stoichiometric experiments and computational studies, a mechanism which proceeds via a trans-dihydride intermediate is proposed. The structure of the hydride complexes was also confirmed by X-ray crystallography.
Gorgas, Nikolaus,St?ger, Berthold,Veiros, Luis F.,Kirchner, Karl
p. 2664 - 2672
(2016/04/26)

Green, Multi-Gram One-Step Synthesis of Core–Shell Nanocomposites in Water and Their Catalytic Application to Chemoselective Hydrogenations
We devise a new and green route for the multi-gram synthesis of core–shell nanoparticles (NPs) in one step under organic-free and pH-neutral conditions. Simply mixing core and shell metal precursors in the presence of solid metal oxides in water allowed for the facile fabrication of small CeO2-covered Au and Ag nanoparticles dispersed on metal oxides in one step. The CeO2-covered Au nanoparticles acted as a highly efficient and reusable catalyst for a series of chemoselective hydrogenations, while retaining C=C bonds in diverse substrates. Consequently, higher environmental compatibility and more efficient energy savings were achieved across the entire process, including catalyst preparation, reaction, separation, and reuse.
Urayama, Teppei,Mitsudome, Takato,Maeno, Zen,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
supporting information
p. 17962 - 17966
(2016/12/16)

Chemoselective Transfer Hydrogenation of Aldehydes and Ketones with a Heterogeneous Iridium Catalyst in Water
Ir nanocatalyst Ir@CN was prepared by pyrolysis of the IrCl3 complex with 1,10-phenanthroline in the activated carbon. The iridium nanocatalyst Ir@CN was highly selective for the transfer hydrogenation of aldehydes and ketones including benzaldehyde derivatives, and the hydrogenative alkylation of C=O bonds was suppressed effectively. The iridium nanocatalyst Ir@CN is a heterogeneous catalyst and can be reused several times for the transfer hydrogenation of aldehydes and ketones.
Wang, Zhi,Huang, Lei,Geng, Longfei,Chen, Rizhi,Xing, Weihong,Wang, Yong,Huang, Jun
p. 1008 - 1013
(2015/03/05)

A new designed hydrazine group-containing ruthenium complex used for catalytic hydrogenation of esters
A hydrazine group-containing nitrogen-phosphine ligand and corresponding ruthenium complexes were synthesized. When these complexes were used for hydrogenation of esters, excellent performance was observed (TON up to 17 200). A wide substrate scope was suitable for this catalytic system.
Tan, Xuefeng,Wang, Qingli,Liu, Yuanhua,Wang, Fangyuan,Lv, Hui,Zhang, Xumu
p. 12193 - 12196
(2015/07/27)

Highly efficient tetradentate ruthenium catalyst for ester reduction: Especially for hydrogenation of fatty acid esters
A new tetradentate ruthenium complex has been developed for hydrogenation of esters. The catalysts structure features a pyridinemethanamino group and three tight chelating five-membered rings. The structure character is believed to be responsible for its high stability and high carbonylation-resistant properties. Thus, this catalyst shows outstanding performance in the catalytic hydrogenation of a variety of esters, especially for fatty acid esters, which may be used in practical applications. New insight on designing hydrogenation catalyst for reducing esters to alcohols has been provided through theoretical calculations.
Tan, Xuefeng,Wang, Yan,Liu, Yuanhua,Wang, Fangyuan,Shi, Liyang,Lee, Ka-Ho,Lin, Zhenyang,Lv, Hui,Zhang, Xumu
supporting information
p. 454 - 457
(2015/03/05)

HYDROGENATION OF ESTERS WITH FE/TRIDENTATE LIGANDS COMPLEXES
The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of Fe complexes with tridentate ligands, having one amino or imino coordinating group and two phosphino coordinating groups, in hydrogenation processes for the reduction of ketones, aldehydes, esters or lactones into the corresponding alcohol or diol, respectively.
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(2015/07/07)