Synthesis of new triarylphosphine ligand and their application in styrene hydroformylation

Guo, Yu; Fu, Haiyan; Chen, Hua; Li, Xianjun

doi:10.1016/j.catcom.2008.02.017

Cited by 30 publications

(11 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Interestingly -and in contrast to the model substrate PhI -in many cases the expected [PAr 4 ]I salt was accompanied by significant quantities of the tertiary phosphine PAr 3 in the product mixture, often with high selectivity for the latter. In particular, the reaction of (o-tol)I (o-tol = 2-methylphenyl) was found to give exclusively the tertiary phosphine (o-tol)3P (Table 2, entry 4), which has found extensive use as a bulky ligand in transition metal coordination chemistry and related catalysis, [6][7][8][9][10][11] and could be cleanly isolated from a scaled up reaction mixture by simple sublimation (71% isolated yield, 216 mg; Supplementary Method 5). Other substituted derivatives of [Ph 4 P]I and (otol) 3 P could also be isolated using similar procedures (Table 2, entries 2, 3, 5, 6, Supplementary Methods 3, 4, 6, 7), although in practice this was limited to examples that proceeded with good conversion and high selectivity.…”

Section: Reaction Scopementioning

confidence: 99%

“…3 Notable families of industrially-relevant organophosphorus species prepared from P 4 include triarylphosphines (Ar 3 P) and salts of the related quaternary phosphonium cations (Ar 4 P + ). The former are widely used both in organic chemistry (notably in the classic Wittig reaction) 4,5 and as ligands for metal complexes, [6][7][8][9][10][11] including the homogeneous catalysts for numerous landmark chemical reactions (e.g. industrial-scale hydroformylation).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Direct catalytic transformation of white phosphorus into arylphosphines and phosphonium salts

et al. 2019

View full text Add to dashboard Cite

Phosphorus compounds are ubiquitous in the chemical sciences, finding applications throughout industry and academia. Of particular interest to synthetic chemists are organophosphorus compounds, which contain P-C bonds. However, state-of-the-art processes for the synthesis of these important materials rely on an inefficient, stepwise methodology involving initial oxidation of white phosphorus (P 4 ) with hazardous chlorine gas and the subsequent displacement of chloride ions. Catalytic P 4 organofunctionalisation reactions have remained elusive, as they require multiple P-P bond breaking and P-C bond formation events to break down the P 4 core, all of which must occur in a controlled manner. Herein, we describe an efficient transition metalcatalyzed process capable of forming P-C bonds from P 4 . Using blue light photocatalysis, this method directly affords valuable triarylphosphines and tetraarylphosphonium salts in a single reaction step.The academic, industrial and societal importance of phosphorus chemistry is difficult to overstate. Phosphorus is one of the six essential 'biogenic elements' required in large quantities by every living organism, and synthetic phosphorus compounds find myriad industrial and commercial applications due to their diverse array of useful chemical, physical and biological properties. 1 This importance is reflected in the fact that white phosphorus (P 4 ) is currently produced on an estimated scale of >1 Mt / year. 2 P 4 is by far the most reactive and industrially-relevant form of elemental phosphorus, and acts as the common precursor from which effectively all synthetic phosphorus-containing species are ultimately Users may view, print, copy, and download text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use:

show abstract

Section: Reaction Scopementioning

confidence: 99%

mentioning

confidence: 99%

Direct catalytic transformation of white phosphorus into arylphosphines and phosphonium salts

et al. 2019

View full text Add to dashboard Cite

show abstract

“…A wide variety of phosphorus-donor ligands have been evaluated in Rh catalysts for the hydroformylation of alkenes [1,2]. Among the most active and selective catalysts are Rh complexes of phosphite and bis(phosphite) ligands [3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and coordination chemistry of a new phosphite–ether ligand: The effects of alkali metal salts and the ligand/Rh molar ratio on the catalytic activity and regioselectivity of a Rh(I) complex of this ligand in the hydroformylation of styrene

Kaisare¹,

Owens²,

Valente³

et al. 2010

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

“…For instance, para-methyl-and para-methoxy-substituted vinylarenes afforded relatively low regioselectivities towards the branched aldehydes, resectively, compared to styrene as well as the halo substituted para-vinylarene. 2-Vinylnaphthalene was considered as hardly reactive in toluene/water biphase system because of the large steric hindrance and the extremely low water solubility [45][46][47][48] . To our delight, 2-vinylnaphthalene was also quite reactive in the present system, giving 98% conversion, high chemoselectivity (>99%) and a b/l ratio of 6.2:1 with prolonged time (36 h).…”

Section: Resultsmentioning

confidence: 99%

Phosphorus coordinated Rh single-atom sites on nanodiamond as highly regioselective catalyst for hydroformylation of olefins

Gao

Liang

et al. 2021

Preprint

View full text Add to dashboard Cite

Single-atom Rh catalysts present superior activity relative to homogeneous catalyst in olefins hydroformylation, yet with limited success in regioselectivity control. In the present work, we develop a novel phosphorus coordinated Rh1 single-atom catalyst with nanodiamond as support. Benefiting from this unique structure, the catalyst exhibits excellent activity and regioselectivity for the hydroformylation of arylethylenes with wide substrate generality, i.e., with high conversion (>99%) and high regioselectivity (>90%), which is comparable with the homogeneous counterparts. The coordination interaction between Rh1 and surface phosphorus species is clarified by 31P solid-state NMR and X-ray absorption spectroscopy (XAS). Rh single atoms are firmly anchored over nanodiamond through Rh-P bonds, guaranteeing good stability in the hydroformation of styrene even after six runs. Finally, by using this new catalyst, two kinds of pharmaceutical molecules, Ibuprofen and Fendiline, are synthesized efficiently with high yields, demonstrating a new prospect of single-atom catalyst in pharmaceutical synthesis.

show abstract

Synthesis of new triarylphosphine ligand and their application in styrene hydroformylation

Cited by 30 publications

References 12 publications

Direct catalytic transformation of white phosphorus into arylphosphines and phosphonium salts

Direct catalytic transformation of white phosphorus into arylphosphines and phosphonium salts

Synthesis, characterization and coordination chemistry of a new phosphite–ether ligand: The effects of alkali metal salts and the ligand/Rh molar ratio on the catalytic activity and regioselectivity of a Rh(I) complex of this ligand in the hydroformylation of styrene

Phosphorus coordinated Rh single-atom sites on nanodiamond as highly regioselective catalyst for hydroformylation of olefins

Contact Info

Product

Resources

About