The Rh, Co, Ru metal-catalyzed hydroformylation of hex-1-ene using triphenylphosphine, triphenylarsine and triphenylantimony as ligands

Srivastava, Vivek; Shukla, Ram S.; Bajaj, Hari C.; Jasra, Raksh V.

doi:10.1016/j.apcata.2004.11.040

Cited by 27 publications

(10 citation statements)

References 27 publications

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“…It has been reported that the more electron-withdrawing the substituents in the ligand, the more basic the catalyst becomes and hence the less it favours high hydroformylation rates. 13,29,30 This is not observed in the results except the slight drop in the aldehyde chemoselectivity with 9 in the fourth recycle, which could be due to altering of structure of the catalyst.…”

Section: Dalton Transactions Papermentioning

confidence: 73%

Recoverable and recyclable water-soluble sulphonated salicylaldimine Rh(i) complexes for 1-octene hydroformylation in aqueous biphasic media

2015

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A series of water-soluble Rh(i) mononuclear complexes of general formula: [Rh(sulphsal-X-R)(COD)] [sulphsal = sulphonated salicylaldimine, COD = cyclooctadiene; where R = H, Cl, CH3 and X = H, (t)Bu] have been synthesized. All the compounds were characterised using various spectroscopic and analytical techniques such as nuclear magnetic resonance spectroscopy, infrared spectroscopy, single crystal X-ray diffraction (for complex ) and mass spectrometry. All the compounds display excellent water-solubility at room temperature and were tested as catalyst precursors in the aqueous biphasic hydroformylation of 1-octene. The catalysts could be easily recovered by phase separation and were used up to 5 times without any significant loss in activity and 1-octene conversion. Very high yields of the expected aldehydes were obtained without addition of any phase transfer agents, co-solvents or hydrophobic ligands. Excellent aldehyde chemoselectivity is observed for all the catalysts but this varied each time the catalysts were recycled, with the formation of a small amount of internal olefins. ICP-OES and mercury poisoning experiments show that a combination of homogeneous catalysis and catalysis mediated by nanoparticles is taking place in these systems.

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Section: Dalton Transactions Papermentioning

confidence: 73%

Recoverable and recyclable water-soluble sulphonated salicylaldimine Rh(i) complexes for 1-octene hydroformylation in aqueous biphasic media

2015

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“…The synthesis of complex RhCl(AsPh 3 ) 3 , an analogue of RhCl(PPh 3 ) 3 , has been reported by Mague and Wilkinson, 12 but they have not studied hydroformylation with this complex. In comparative studies 13 on hydroformylation of 1-hexene with Rh, Co, and Ru complexes having group V elements ligands (PPh 3 , AsPh 3 , and SbPh 3 ), we recently observed similar activities for Rh/ PPh 3 and Rh/AsPh 3 catalyst systems with the former showing higher n/iso ratio of aldehydes. Due to its commercial significance, kinetics and mass transfer analysis of the hydroformylation reaction using PPh 3 and its derivatives as a ligand are reported.…”

Section: Introductionmentioning

confidence: 90%

Kinetic Studies on the Hydroformylation of 1-Hexene Using RhCl(AsPh₃)₃ as a Catalyst

Srivastava

Sharma

Shukla

et al. 2005

Ind. Eng. Chem. Res.

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The detail kinetic study of 1-hexene hydroformylation using RhCl(AsPh3)3 as a homogeneous catalyst has been investigated. The present kinetic study involves the effect of concentrations of 1-hexene and catalyst, partial pressures of CO and H2, agitation speed, and temperature on the rate of hydroformylation. Additionally, the studies of deactivation of the catalyst RhCl(AsPh3)3 with temperature have also been done. It was observed that the rates of hydroformylation reaction were increased on increasing the initial concentrations of 1-hexene, catalyst, and partial pressures of CO and H2 at lower ranges. The activation energy was found to be 42.74 kJ/mol. A nonlinear semiempirical kinetic model was also developed to be the best fit with 11.6% error.

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“…In many transition metal-catalyzed reactions arsine ligands proved to be more active or selective ligands than phosphines. Some of these reactions employed Ph3As as ligand, including Stille 1] and Suzuki-Miyaura coupling processes [2], Negishi reaction [3], Heck and related reactions [4], Sonogashira [5], cross-coupling with arylsilanol [6], hydroformylation of terminal alkenes [7], carbonylations [8], polymerizations [9], and Buchwald coupling reactions 10. Moreover, biologically active molecules were synthesized by Pd-catalyzed reactions using Ph3As as ligand [11].…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Arsination Reactions and their Applications on the Synthesis of Arsine Ligands

Uberman

Martín

2018

COC

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In the synthesis of new ligands for metal-catalyzed reactions, arsine are attracting particular attention, because arsine ligands have been shown to be better ligands than structurally related phosphines in several catalyzed reactions. However, the synthesis and applications of arsine ligands is not widely extended in the literature. One of the main barriers to develop new arsine ligands is found in the synthetic methodologies to obtain arsine compounds. Therefore, to expand the applications of arsine ligands it is necessary to develop new synthetic strategies. To improve the classic arsination reactions metal-catalyzed C-As bond formation reactions appears to be a promising approach. This article highlights the palladium-catalyzed arsination reactions, providing the synthetic approaches used to obtain arsines. In addition, the few described examples of other metal-catalyzed arsination reactions are included. The synthesis of structurally diverse arsine ligands by catalyzed arsination reactions is summarized, as well as the most relevant issues of their applications in homogeneous catalysis.

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The Rh, Co, Ru metal-catalyzed hydroformylation of hex-1-ene using triphenylphosphine, triphenylarsine and triphenylantimony as ligands

Cited by 27 publications

References 27 publications

Recoverable and recyclable water-soluble sulphonated salicylaldimine Rh(i) complexes for 1-octene hydroformylation in aqueous biphasic media

Recoverable and recyclable water-soluble sulphonated salicylaldimine Rh(i) complexes for 1-octene hydroformylation in aqueous biphasic media

Kinetic Studies on the Hydroformylation of 1-Hexene Using RhCl(AsPh₃)₃ as a Catalyst

Palladium-Catalyzed Arsination Reactions and their Applications on the Synthesis of Arsine Ligands

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The Rh, Co, Ru metal-catalyzed hydroformylation of hex-1-ene using triphenylphosphine, triphenylarsine and triphenylantimony as ligands

Cited by 27 publications

References 27 publications

Recoverable and recyclable water-soluble sulphonated salicylaldimine Rh(i) complexes for 1-octene hydroformylation in aqueous biphasic media

Recoverable and recyclable water-soluble sulphonated salicylaldimine Rh(i) complexes for 1-octene hydroformylation in aqueous biphasic media

Kinetic Studies on the Hydroformylation of 1-Hexene Using RhCl(AsPh3)3 as a Catalyst

Palladium-Catalyzed Arsination Reactions and their Applications on the Synthesis of Arsine Ligands

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Kinetic Studies on the Hydroformylation of 1-Hexene Using RhCl(AsPh₃)₃ as a Catalyst