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Catalysis Involving Fluorous Phases: Fundamentals and Directions for Greener Methodologies

Part 1. Homogeneous Catalysis

  1. John A. Gladysz

Published Online: 15 MAR 2010

DOI: 10.1002/9783527628698.hgc002

Handbook of Green Chemistry

Handbook of Green Chemistry

How to Cite

Gladysz, J. A. 2010. Catalysis Involving Fluorous Phases: Fundamentals and Directions for Greener Methodologies. Handbook of Green Chemistry. 1:2:17–38.

Author Information

  1. Texas A&M University, Department of Chemistry, USA

Publication History

  1. Published Online: 15 MAR 2010

Chemistry Terms

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Abstract

This article briefly reviews the fundamentals of fluorous chemistry, with an emphasis on aspects most relevant to catalysis. The development of “greener” fluorous solvents and ponytails (phase tags) is described. Protocols that minimize the use of fluorous solvents are emphasized. Some of these exploit the highly temperature dependent solubilites of fluorous compounds in organic solvents, which can be fine-tuned by varying the length and number of the (CF2)n segments in the ponytails. Suitably designed fluorous catalysts can thus be employed under homogeneous conditions at elevated temperatures, and recovered by solid/liquid phase separation at lower temperatures. Fluorous solid supports such as fluoropolymers and fluorous silica gel can be used to aid the recovery of small catalyst quantities, and render phase separation more efficient. The use of CO2 pressure as a non-thermal solubility trigger, and catalyst recovery by solid phase extraction using non-fluorous solvents, are also detailed.

Keywords:

  • fluorous phases;
  • fluorine;
  • ponytail;
  • homogeneous catalysis;
  • green chemistry

Featured Compounds

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  1. 1 - 28
Compound 1
Molecular Weight:866.127
Molecular Formula:C17F34O
InChIKey:HPQWUGVNUHTGQQ-UHFFFAOYSA-N
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Compound 2
Molecular Weight:1761.1
Molecular Formula:C36H13F63Sn
InChIKey:TYEVHCDXCYFGEG-UHFFFAOYSA-N
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Compound 3
Molecular Weight:1372.3086
Molecular Formula:C30H12F51P
InChIKey:XUFHQDUCMQTBMA-UHFFFAOYSA-N
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Compound 4
Molecular Weight:1414.3883
Molecular Formula:C33H18F51P
InChIKey:AVYIPNHAVMTSEM-UHFFFAOYSA-N
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Compound 5
Molecular Weight:1846.3097
Molecular Formula:C38H16F64IP
InChIKey:WHVVIYRXIFMSMA-UHFFFAOYSA-M
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Compound 6
Molecular Weight:1158.061
Molecular Formula:C26H5BF42O2
InChIKey:ZYJSSPSJJJYJIT-UHFFFAOYSA-N
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Compound 7
Molecular Weight:1126.338
Molecular Formula:C23H3F37O5S2
InChIKey:FKYSSXVSWUAILS-UHFFFAOYSA-N
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Compound 8
Molecular Weight:3425.42
Molecular Formula:C64H32Cl4F104O2Sn4
InChIKey:HTNQIUPXLCOKGD-UHFFFAOYSA-J
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Compound 9
Molecular Weight:3113.79
Molecular Formula:C48F102N3O12S6Yb
InChIKey:RAFINEOEBDXYPM-UHFFFAOYSA-N
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Compound 11
Molecular Weight:2195.454
Molecular Formula:C57H49CuF68N3O4
InChIKey:PNKYHMGVRIQCSD-UHFFFAOYSA-L
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Compound 12
Molecular Weight:1669.7411
Molecular Formula:C53H34F46NO5P
InChIKey:FCWHTUGQRMFRMJ-DEOSSOPVSA-N
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Compound 13
Molecular Weight:1416.3352
Molecular Formula:C31H11F51O4
InChIKey:IVYJTPPYTQPZBD-VAYJURFESA-N
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Compound 14
Molecular Weight:594.1599
Molecular Formula:C13H7F21O2
InChIKey:JRJPHUAHPMPZNE-UHFFFAOYSA-N
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Compound 15
Molecular Weight:Not Available
Molecular Formula:(CF2)n(CF2)n(CF2)n(CF2)n(CF2)n(CF2)n(CF2)n(CF2)n(C)nC27H36ClF29P3Rh
InChIKey:MXWSWBPSLIEMFE-UHFFFAOYSA-M
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Compound 18
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21
Molecular Weight:778.2674
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 19
Molecular Weight:1173.5122
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 20
Molecular Weight:521.2656
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 22
Molecular Weight:3474.77
Molecular Formula:C102H72Cl2F102P2Pd
InChIKey:LWNYWSCXIJSXBG-UHFFFAOYSA-L
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Compound 23
Molecular Weight:3090.31
Molecular Formula:C84H36Cl2F90O6P2Pd
InChIKey:GFZPUECSQAGPQP-UHFFFAOYSA-L
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Compound 24
Molecular Weight:1858.0528
Molecular Formula:C32F60O8Rh2
InChIKey:OUSBSBBCBVJRBU-UHFFFAOYSA-J
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Compound 25
Molecular Weight:1438.91
Molecular Formula:C42H24ClF39PRh
InChIKey:ZSKDDXCPJQITHR-UHFFFAOYSA-M
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Compound 26
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 27
Molecular Weight:1099.42
Molecular Formula:C32H15ClF26PdS2
InChIKey:HEWFTHSKKOEART-UHFFFAOYSA-M
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Compound 28
Molecular Weight:1476.9766
Molecular Formula:C30H6F52NiO4
InChIKey:LANTYGLVXFJPKX-UHFFFAOYSA-N
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Compound 29
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 30
Molecular Weight:Not Available
Molecular Formula:(CH2)m(CH2)mC28H24F34N2O4
InChIKey:VOHGYGXAVMFCDM-UHFFFAOYSA-N
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Compound 31
Molecular Weight:640.4794
Molecular Formula:C27H25F13N2O
InChIKey:YXSQXZCOMHKRLC-IBGZPJMESA-N
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