Synthesis of RuCl2(xantphos)L (L = PPh3, P(OPh)3, DMSO) complexes, and their catalytic activity for the addition of carboxylic acids onto olefins

Higashi, Shoko; Takenaka, Hiroto; Ito, Yoshihiko; Oe, Yohei; Ohta, Tetsuo

doi:10.1016/j.jorganchem.2015.04.016

Cited by 8 publications

(5 citation statements)

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“…As a result, 3a was obtained in 82% yield with quantitative conversion (entry 13). Since it is known that the complexation of Xantphos and RuCl2(PPh3)3 proceeds nicely to afford the Xantphos-Ru complex, 13 we tested the combination catalyst of Xantphos and RuCl2(PPh3)3. We finally found that this catalysis afforded 3a in almost quantitative yield (entry 14).…”

Section: Resultsmentioning

confidence: 99%

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Ruthenium-Catalyzed Hydroxyethylation of Cyclic Amines with Ethylene Glycol

Oe¹,

Nakamura²,

Tomioka³

et al. 2019

HETEROCYCLES

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Section: Resultsmentioning

confidence: 99%

“…NMR spectra were recorded with Bruker Ascend 400 spectrometer (400 MHz) spectrometers by using TMS ( = 0 ppm) as an internal standard for 1 H NMR and CDCl3 ( = 77 ppm) for 13 17 and Cp*RuCl2(PPh3) 18 were synthesized according to literature protocols.…”

Section: General Informationmentioning

confidence: 99%

Ruthenium-Catalyzed Hydroxyethylation of Cyclic Amines with Ethylene Glycol

Oe¹,

Nakamura²,

Tomioka³

et al. 2019

HETEROCYCLES

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“…An ubiquitous iron catalysis has been reported by Sakakura et al, where the unstable ester such as acrylates can be synthesized under the solventfree reaction conditions (entry 4) [145]. Modified ruthenium(II) catalysis including xantphos ligand improved the scope of substrates of alkenes compared to that with ruthenium(III) catalyst to afford the corresponding esters in up to 99% yield by Oe et al (entry 5) [146].…”

Section: The Addition Of Carboxylic Acids Onto Alkynesmentioning

confidence: 99%

Recent Advances in the Synthesis of Carboxylic Acid Esters

Matsumoto¹,

Yanagi²,

Oe³

2018

Carboxylic Acid - Key Role in Life Sciences

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In this chapter, recent advances in the synthesis of carboxylic acid esters are summarized based on the utilization of carboxylic acids as electrophiles or nucleophiles in reactions. Condensation reagents or catalysts connect the carboxylic acids with the alcohols to afford the corresponding esters, together with the formation of 1 equiv. of H 2 O, in which the carboxylic acids can be regarded as the electrophile. In contrast, the carboxylate ion intermediates derived from the carboxylic acids react with alkyl halides, carbocations, or their equivalents to produce the esters, in which the carboxylate ions from the carboxylic acids can be regarded as the nucleophile. This chapter mainly introduces the recent progress in this field of the formation of esters, based on the classification of the role of carboxylic acids in reactions.

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“…A common way to produce ruthenacarboranes bearing chelate diphosphine ligands with wide bite angles is the reaction of the corresponding RuCl 2 (PPh 3 )(diphosphine) with the salt of the nido-carborane [4]. The reaction of the known RuCl 2 (PPh 3 )(Xantphos) [8] with K + [nido-7,8-C 2 B 9 H 12 ] − in benzene did not give the desired product neither at room temperature no on heating. This fact may be explained by the action of Xantphos as a k 3 -ligand strongly occupying three equatorial sites in the ruthenium coordination sphere [9].…”

Section: Synthesis Of Novel Ruthenacarboranesmentioning

confidence: 99%

12-Vertex closo-3,1,2-Ruthenadicarbadodecaboranes with Chelate POP-Ligands: Synthesis, X-ray Study and Electrochemical Properties

et al. 2022

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A class of so-called POP ligands (Xanthos, NiXantphos, DPEphos) are of a great interest to the coordination chemistry due to their wide P-M-P bite angles and ability to show either κ2- or κ3-binding modes. Such κ2–κ3-rearrangement is valuable for catalytic application and internal stabilization of intermediates. To widen the scope of ruthenium-based catalysts for Atom Transfer Radical Polymerization (ATRP) two new approaches to the synthesis of closo-ruthenacarboranes with aforementioned POP ligands were developed and six new 17-e (3,3-(POP)-3-Cl-closo-3,1,2-RuC2B9H11; 2, 4, 7) and 18-e (3,3-(POP)-3-NCCH3-closo-3,1,2-RuC2B9H11; 3, 5, 8) clusters were synthesized and characterized by means of NMR or ESR spectroscopy, MALDI mass-spectrometry and single crystal X-ray diffraction studies. The unique 18-e complex of Ru(II) with dioxygen ligand 3,3-(DPEphos)-3-(η2-O2)-closo-3,1,2-RuC2B9H11 (9) was isolated and characterized by X-ray diffraction. It was shown that aforementioned POP ligands coordinate to ruthenium by two phosphorus atoms in a κ2-fashion. The performed electrochemical studies have shown reversible Ru(II)-Ru(III) transition making the complexes suitable for application in catalysis of polymerization. The test experiments on methyl methacrylate (MMA) polymerization indicate the proceeding of the process in according with an ATRP mechanism.

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Synthesis of RuCl2(xantphos)L (L = PPh3, P(OPh)3, DMSO) complexes, and their catalytic activity for the addition of carboxylic acids onto olefins

Cited by 8 publications

References 74 publications

Ruthenium-Catalyzed Hydroxyethylation of Cyclic Amines with Ethylene Glycol

Ruthenium-Catalyzed Hydroxyethylation of Cyclic Amines with Ethylene Glycol

Recent Advances in the Synthesis of Carboxylic Acid Esters

12-Vertex closo-3,1,2-Ruthenadicarbadodecaboranes with Chelate POP-Ligands: Synthesis, X-ray Study and Electrochemical Properties

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