Fluorous Biphasic Catalysis Without Perfluorinated Solvents: Application to Pd‐Mediated Suzuki and Sonogashira Couplings.

Tzschucke, Carl Christoph; Märkert, Christian; Glatz, Heiko; Bannwarth, Willi

doi:10.1002/chin.200314066

Cited by 2 publications

(4 citation statements)

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“…Adsorption (physisorption) of fluorous catalysts on solid fluorous substrates such as fluorous silica or Teflon is another very interesting strategy for efficient and easy recycling of catalysts under conditions that do not require PFCs. Bannwarth et al (Tzschucke et al 2002) and Biffis et al (Biffis et al 2003) were independently the first to show that fluorous catalysts were effectively adsorbed to the fluorous silica surface. These catalysts can then be used as conventional supported catalysts under heterogeneous conditions with the advantage of being separable by simple filtration or decantation.…”

Section: Figure 22 Biphasic Fluorous Catalyst Applied To the Hydrofor...mentioning

confidence: 99%

“…These catalysts can then be used as conventional supported catalysts under heterogeneous conditions with the advantage of being separable by simple filtration or decantation. This methodology has been applied to Suzuki and Sonogashira couplings catalyzed by fluorous Pd-phosphine complexes (Tzschucke et al 2002), and to alcohol silylation catalyzed by Rh-carboxylate complexes (Biffis et al 2003). The supported catalysts retain a high reactivity associated with a low contamination of the final product by the metal (~ 2%).…”

Section: Figure 22 Biphasic Fluorous Catalyst Applied To the Hydrofor...mentioning

confidence: 99%

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Biphasic Chemistry and The Solvent Case

2020

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Fluorous tags and phases for synthesis and catalysis IntroductionThe development of more efficient, rapid and environmentally friendly synthesis processes, whether for the production of high-tonnage compounds, pharmaceutical compounds or on a laboratory scale, is an important objective of current research. Most research efforts focus on optimizing the activity of existing reagents or catalysts or discovering new reactions. However, in a synthesis process, the purification step should not be neglected, as the isolated product yield and the overall energy cost of synthesis depend strongly on the nature and efficiency of the latter (Curran 1998). Methodologies for easily separating or recycling a catalyst, reagent or by-product from a reaction medium are to be encouraged in the context of sustainable chemistry. Ideally, these methods should make it possible to avoid as much as possible chromatographic purifications that consume large amounts of organic solvents, and if possible, distillations, which are costly in terms of energy and can lead to catalyst degradation. The use of liquid (perfluorocarbons) or solid (perfluorinated silicas or Teflon) perfluorinated phases is fully in line with this approach. Perfluorocarbons (PFCs), such as n-perfluorohexane (C6F14), are liquids with extreme physicochemical properties. They are chemically inert, non-toxic and are the most non-polar liquids available. They are both hydrophobic and lipophobic, so they form liquid/liquid two-phase systems at room temperature with most organic solvents. The principle of fluorous chemistry consists of increasing the affinity of catalysts, reagents or substrates for liquid or solid perfluorinated phases, i.e. increasing their fluorophilicity. This is achieved by modifying catalysts, reagents or substrates with perfluoroalkyl fragments called fluorous tags (Ftags). As we will see later, fluorous compounds present in a reaction medium can then Chapter written by Jean-Marc VINCENT.

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Section: Figure 22 Biphasic Fluorous Catalyst Applied To the Hydrofor...mentioning

confidence: 99%

Section: Figure 22 Biphasic Fluorous Catalyst Applied To the Hydrofor...mentioning

confidence: 99%

Biphasic Chemistry and The Solvent Case

2020

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“…The results are as follows: PtCl2(Ph2P n C10F21)2, 0.32 g/L; RhCl(CO)(Ph2P n C10F21)2, 0.40 g/L; IrCl(CO)(Ph2P n C10F21)2, 0.13 g/L; AuCl(Ph2P n C10F21), did not dissolve. Because the fluorine (7) A catalytic hydroalkoxylation of an alkene was demonstrated using gold complex 5, according to the literature [35]. In the presence of a catalytic amount of 5a and AgOTf, the addition reaction of 2-chloroethanol to 1-octene took place to give 2-(2 -chloroethoxy)octane in a good yield (Equation (8)).…”

Section: (4)mentioning

confidence: 99%

“…P-Fluorous phosphine (R 2 PR f ), in which the perfluoroalkyl group is directly bonded to the phosphorus atom, is a hybrid functional phosphine ligand having both "electron-poor" [1] and "fluorous" [2][3][4][5][6][7][8] characteristics. Since strongly electron-withdrawing ligands are known to promote reductive elimination steps in catalytic reactions, the former property may be exploited, not only to optimize known reactions, but also to develop new catalytic reactions [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

P-Fluorous Phosphines as Electron-Poor/Fluorous Hybrid Functional Ligands for Precious Metal Catalysts: Synthesis of Rh(I), Ir(I), Pt(II), and Au(I) Complexes Bearing P-Fluorous Phosphine Ligands

et al. 2017

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P-Fluorous phosphine (R 2 PR f ), in which the perfluoroalkyl group is directly bonded to the phosphorus atom, is a promising ligand because it has a hybrid functionality, i.e., electron-poor and fluorous ligands. However, examples of P-fluorous phosphine-metal complexes are still rare, most probably because the P-fluorous group is believed to decrease the coordination ability of the phosphines dramatically. In contrast, however, we have succeeded in synthesizing a series of P-fluorous phosphine-coordinated metal complexes such as rhodium, iridium, platinum, and gold. Furthermore, the electronic properties of R 2 P n C 10 F 21 are investigated by X-ray analysis of PtCl 2 (Ph 2 P n C 10 F 21 ) 2 and the infrared CO stretching frequency of RhCl(CO)(R 2 P n C 10 F 21 ) 2 . IrCl(CO)(Ph 2 P n C 10 F 21 ) 2 -and AuCl(R 2 P n C 10 F 21 )-catalyzed reactions are also demonstrated.

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Fluorous Biphasic Catalysis Without Perfluorinated Solvents: Application to Pd‐Mediated Suzuki and Sonogashira Couplings.

Cited by 2 publications

References 1 publication

Biphasic Chemistry and The Solvent Case

Biphasic Chemistry and The Solvent Case

P-Fluorous Phosphines as Electron-Poor/Fluorous Hybrid Functional Ligands for Precious Metal Catalysts: Synthesis of Rh(I), Ir(I), Pt(II), and Au(I) Complexes Bearing P-Fluorous Phosphine Ligands

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