From Internal Olefins to Linear Amines: Ruthenium-Catalyzed Domino Water–Gas Shift/Hydroaminomethylation Sequence

Liu, Jie; Kubis, Christoph; Franke, Robert; Jackstell, Ralf; Beller, Matthias

doi:10.1021/acscatal.5b02457

Cited by 49 publications

(23 citation statements)

References 89 publications

(28 reference statements)

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“…[45] Chatani found that, under carbonylation of C-H bonds, fragmentation of the precatalyst Ru3(CO)12 into mononuclear Rucomplexes occurs [46][47][48]. Beller reported precatalytic amounts of Ru3(CO)12 mixed with phosphine ligands in-situ forms a mononuclear species [49][50][51]. Thus, there is significant evidence suggesting that Ru3(CO)12 behaves as a precatalyst for a variety of catalytically active mononuclear Ru-species.…”

Section: P 4 Of 52mentioning

confidence: 99%

Homogeneous Catalysis by Organometallic Polynuclear Clusters

2019

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Homogeneous polynuclear metal clusters constitute a broad class of coordination compounds with important applications in catalysis. The current interest of synthetic chemistry in this field demands the exploration of new strategies to develop catalytic methods that work under mild conditions and maximize atom utilization. This review covers the application of polynuclear clusters of nuclearity ≥3 in homogeneous catalytic processes, with focus on providing an array of examples of various reaction types within cluster catalysis.

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Section: P 4 Of 52mentioning

confidence: 99%

Homogeneous Catalysis by Organometallic Polynuclear Clusters

2019

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“…Current research deals with the application of the watergas shift or reversed water-gas shift reaction using carbon monoxide and water or carbon dioxide and hydrogen in the hydroaminomethylation instead of syngas [31][32][33][34][35]. Eilbracht et al has done research on hydroaminomethylation in synthesizing dendrimers [36][37][38][39].…”

Section: Introductionmentioning

confidence: 99%

Catalyst recycling in the hydroaminomethylation of methyl oleate: A route to novel polyamide monomers

Vorholt

Immohr

Ostrowski

et al. 2016

Euro J Lipid Sci & Tech

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This article describes the development of an effective thermomorphic multicomponent solvent (TMS) system for the production of branched polyamide monomers. In this system, methyl oleate, a renewable from fats and oils, and a functionalized amine are used as starting materials in a tandem catalytic reaction, which merges different reaction steps into a single preparative step. This particular TMS system consisted of a heptane/acetonitrile solvent mixture and made reusing the precious rhodium catalyst possible in three recycle runs. A constant yield of 61–65% was obtained for each run due to low‐catalyst leaching. Fortunately, the catalyst system does not require any additional phosphorous ligands and allows high yields. A scale‐up for the production of 10–11 g of the desired product in each run was realized. Subsequent hydrogenation of the product directly provided an amine ester, which is a valuable polyamide monomer. Practical applications: A method was developed to enable access to primary amines via hydroaminomethylation and hydrogenation. The product, a nitrile ester, is a valuable intermediate for polyamide monomers. This nitrile ester was successfully hydrogenated to an amine ester, which features a potential polyamide monomer directly. A catalyst recycle of the homogeneous rhodium complex within the hydroaminomethylation of methyl oleate and an amino nitrile was successfully carried out, enabling constant homogeneous catalyst activity over the course of three recycle runs. A scale‐up to obtain 10–11 g of the hydroaminomethylation product was realized. A general method is described for the conversion of methyl oleate within a hydroaminomethylation reaction. The catalyst can be recovered and reused. Valuable polyamide intermediates were obtained.

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“…Application References pyridyl phosphines OLEDs [13] Heck coupling [14] metal organic frameworks [15] polymerization of lactides [16] alkene hydroxylation [17] addition reaction [18] ethylene oligomerization [19] synthesis of pyrazolines [20] triazolyl phosphines Suzuki cross coupling [21] asymmetric hydrogenation [22] luminescence [23] hydroformylation [24] pyrazolyl phosphines coordination polymers [25] Heck coupling [26] imidazolyl phosphines Suzuki coupling [27] hydroamination [28] OLEDs [29] ethylene oligomerization [30] amination [31] olefin metathesis [32] hydroformylation [33] pyrrolyl phosphines hydroformylation [34,35] ethylene polymerization [36] oxazolyl phosphines asymmetric cycloaddition [37] asymmetric hydrogenation [38] carbonylation of alkynes [39] allylic substitution [40] asymmetric addition [41] allylic amination [42,43] The presence of soft donor atoms such as phosphorus results in the formation of hemilabile ligands. These are multidentate ligands having hard P-donor and soft N-and/or O-donor atoms [44].…”

Section: Type Of Ligandmentioning

confidence: 99%

Architecture and synthesis of P,N-heterocyclic phosphine ligands

Munzeiwa¹,

Omondi²,

Nyamori³

2020

Beilstein J. Org. Chem.

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Diverse P,N-phosphine ligands reported to date have performed exceptionally well as auxiliary ligands in organometallic catalysis. Phosphines bearing 2-pyridyl moieties prominently feature in literature as compared to phosphines with five-membered N-heterocycles. This discussion seeks to paint a broad picture and consolidate different synthetic protocols and techniques for N-heterocyclic phosphine motifs. The introduction provides an account of P,N-phosphine ligands, and their structural and coordination benefits from combining heteroatoms with different basicity in one ligand. The body discusses the synthetic protocols which focus on P–C, P–N-bond formation, substrate and nucleophile types and different N-heterocycle construction strategies. Selected references are given in relation to the applications of the ligands.

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From Internal Olefins to Linear Amines: Ruthenium-Catalyzed Domino Water–Gas Shift/Hydroaminomethylation Sequence

Cited by 49 publications

References 89 publications

Homogeneous Catalysis by Organometallic Polynuclear Clusters

Homogeneous Catalysis by Organometallic Polynuclear Clusters

Catalyst recycling in the hydroaminomethylation of methyl oleate: A route to novel polyamide monomers

Architecture and synthesis of P,N-heterocyclic phosphine ligands

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