Abstract
The application of fluorous phosphine-modified catalysts for the hydrogenation of olefins is reviewed.
Keywords
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsAbbreviations
- FBC:
-
Fluorous biphasic catalysis
- FBS:
-
Fluorous biphasic system
- FC-72:
-
Mixture of perfluorohexanes
- NMR:
-
Nuclear magnetic resonance
- PFMCH:
-
Perfluoromethylcyclohexane
- TOF:
-
Turnover frequency; turnover number per unit time
- TON:
-
Turnover number of moles of substrate that a mole of catalyst can convert before becoming inactivated
References
Oro LA (2003) Hydrogenation – homogeneous. In: Horváth IT (ed) Encyclopedia of catalysis, vol 4. Wiley-Interscience, New York, pp 55–107
Osborn JA, Jardine FH, Young JF, Wilkinson G (1966) The preparation and properties of tris(triphenylphosphine)halogenorhodium(I) and some reactions thereof including catalytic homogeneous hydrogenation of olefins and acetylenes and their derivatives. J Chem Soc A:1711–1732
Halpern J, Wong CS (1973) Hydrogenation of tris(triphenylphosphine)chlororhodium(I). Chem Commun:629
Halpern J (1981) Mechanistic aspects of homogeneous catalytic hydrogenation and related processes. Inorg Chim Acta 50:11–19
Jardine FH (1982) Carbonylhydrido tris(triphenylphosphine)rhodium(I). Polyhedron 1:569–605
Sanfilippo D, Rylander PN (2009) Ullmann’s encyclopedia of industrial chemistry
Cornil B, Herrmann WA (1998) Aqueous phase organometallic catalysis. Wiley-VCH, Weinheim
Horváth IT, Rábai J (1994) Facile catalyst separation without water. Fluorous biphase hydroformylation of olefines. Science 266:72–75
Horváth IT (1998) Fluorous biphase chemistry. Acc Chem Res 31:641–650
Gladysz JA, Curran DP, Horváth IT (2004) Handbook of fluorous chemistry. Wiley-VCH, Weinheim
Juliette JJJ, Horvath IT, Gladysz JA (1997) Transition metal catalysis in fluorous media: practical application of a new immobilization principle to rhodium-catalyzed hydroboration. Angew Chem Int Ed Engl 36:1610–1612
Rutherford D, Juliette JJJ, Rocaboy C, Horváth IT et al (1998) Transition metal catalysis in fluorous media: application of a new immobilization principle to rhodium-catalyzed hydrogenation of alkenes. Catal Today 42:381–388
Meakin P, Jesson JP, Tolman CA (1972) The nature of chlorotris(triphenylphosphine)rhodium in solution and its reaction with hydrogen. J Chem Soc A 94:3270–3272
Goetheer ELV, Verkerk AW, van den Broeke LJP, de Wolf E et al (2003) Membrane reactor for homogeneous catalysis in supercritical carbon dioxide. J Catal 219:126–133
Bergbreiter DE, Franchina JG, Case BL (2000) Fluoroacrylate-bound fluorous-phase soluble hydrogenation catalysts. Org Lett 2:393–395
Richter B, Spek AL, van Koten G, Deelman BJ (2000) Fluorous versions of Wilkinson’s catalyst. Activity in fluorous hydrogenation of 1-alkenes and recycling by fluorous biphasic separation. J Am Chem Soc 122:3945–3951
Richter B, Deelman BJ, van Koten G (1999) Fluorous biphasic hydrogenation of 1-alkenes using novel fluorous derivatives of Wilkinson’s catalyst. J Mol Catal A Chem 145:317–321
van den Broeke J, de Wolf E, Deelman BJ, van Koten G (2003) Enhanced hydrogenation activity and recycling of cationic rhodium diphosphine complexes through the use of highly fluorous and weakly-coordinating tetraphenylborate anions. Adv Synth Catal 345:625–634
de Wolf E, Spek AL, Kuipers BWM, Philipse AP et al (2002) Fluorous derivatives of Rh(COD)(dppe) BX4 (X = F, Ph): synthesis, physical studies and application in catalytic hydrogenation of 1-alkenes and 4-alkynes. Tetrahedron 58:3911–3922
Hope EG, Kemmitt RDW, Paige DR, Stuart AM (1999) The rhodium catalysed hydrogenation of styrene in the fluorous biphase. J Fluor Chem 99:197–200
Hope EG, Sherrington J, Stuart AM (2006) Supported fluorous phase catalysis on PTFE, fluoroalkylated micro- and meso-porous silica. Adv Synth Catal 348:1635–1639
Audic N, Dyer PW, Hope EG, Stuart AM et al (2010) Insoluble perfluoroalkylated polymers: new solid supports for supported fluorous phase catalysis. Adv Synth Catal 352:2241–2250
Ablan CD, Hallett JP, West KN, Jones RS et al (2003) Use and recovery of a homogeneous catalyst with carbon dioxide as a solubility switch. Chem Commun:2972–2973
Soós T, Bennett BL, Rutherford D, Barthel-Rosa LP et al (2001) Synthesis, reactivity, and metal complexes of fluorous triarylphosphines of the formula P(p-C6H4(CH2)3(CF2)n-1CF3)3 (n = 6, 8, 10). Organometallics 20:3079–3086
Sinou D, Maillard D, Aghmiz A, i-Bulto AMM (2003) Rhodium-catalyzed hydrogenation of alkenes by rhodium/tris(fluoroalkoxy)phosphane complexes in fluorous biphasic system. Adv Synth Catal 345:603–611
Chechik V, Crooks RM (2000) Dendrimer-encapsulated Pd nanoparticles as fluorous phase-soluble catalysts. J Am Chem Soc 122:1243–1244
Yılmaz F, Özer M, Kani I, Bekaroglu Ö (2009) Catalytic activity of a thermoregulated, phase-separable Pd(II)-perfluoroalkylphthalocyanine complex in an organic/fluorous biphasic system: hydrogenation of olefins. Catal Lett 130:642–647
Scheuermann GM, Thomann R, Mulhaupt R (2009) Catalysts based upon organoclay with tunable polarity and dispersion behavior: new catalysts for hydrogenation, C–C coupling reactions and fluorous biphase catalysis. Catal Lett 132:355–362
Kani I, Sisman F (2006) Synthesis and catalytic activity of perfluoroalkylated pyridine-palladium(II) complex toward olefin hydrogenation in scCO2 and conventional organic solvents. J Mol Catal A Chem 259:142–149
West KN, Hallett JP, Jones RS, Bush D et al (2004) CO2-induced miscibility of fluorous and organic solvents for recycling homogeneous catalysts. Ind Eng Chem Res 43:4827–4832
Bergbreiter DE, Chandran R (1987) Polyethylene-bound rhodium(I) hydrogenation catalysts. J Am Chem Soc 109:174–179
Malosh TJ, Wilson SR, Shapley JR (2009) Binuclear ruthenium complexes of fluorous phosphine ligands: synthesis, properties, and biphasic catalytic activity. Crystal structure of [Ru(μ-O2CMe)(CO)2P(CH2CH2(CF2)5CF3)3]2. J Organomet Chem 694:3331–3337
Noyori R (1994) Asymmetric catalysis in organic synthesis. Wiley, New York
Franco G, Leitner W (1999) Highly regio- and enantio-selective rhodium-catalysed asymmetric hydroformylation without organic solvents. Chem Commun:1663–1664
Birdsall DJ, Hope EG, Stuart AM, Chen W et al (2001) Synthesis of fluoroalkyl-derivatised BINAP ligands. Tetrahedron Lett 42:8551–8553
Hu Y, Birdsall DJ, Stuart AM, Hope EG et al (2004) Ruthenium-catalysed asymmetric hydrogenation with fluoroalkylated BINAP ligands in supercritical CO2. J Mol Catal A Chem 219:57–60
Horn J, Bannwarth W (2007) Repetitive application of a fluorous chiral BINAP-Ru complex in the asymmetric hydrogenation of olefins. Eur J Org Chem:2058–2063
Burgemeister K, Francio G, Huglc H, Leitner W (2004) Enantioselective hydrogenation of polar substrates in inverted supercritical CO2/aqueous biphasic media. Chem Commun:6026–6028
Burgemeister K, Francio G, Gego VH, Greiner L et al (2007) Inverted supercritical carbon dioxide/aqueous biphasic media for rhodium-catalyzed hydrogenation reactions. Chem Eur J 13:2798–2804
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2011 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Zhao, X., He, D., Mika, L.T., Horváth, I.T. (2011). Fluorous Hydrogenation. In: Horváth, I. (eds) Fluorous Chemistry. Topics in Current Chemistry, vol 308. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_281
Download citation
DOI: https://doi.org/10.1007/128_2011_281
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-25233-4
Online ISBN: 978-3-642-25234-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)