The heck reaction in ionic liquids: Progress and challenges

Molecules

Volumn 15, Issue 4, 2010, Pages 2211-2245

  Bellina, Fabio ^a   Chiappe, Cinzia ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

Heck reaction; Ionic liquids; Pd catalyst; Selectivity

Indexed keywords

IONIC LIQUID; METAL; SOLVENT;

CATALYSIS; CHEMISTRY; ENVIRONMENT; REVIEW;

CATALYSIS; ENVIRONMENT; IONIC LIQUIDS; METALS; SOLVENTS;

EID: 77951838387     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15042211     Document Type: Review

References (88)

1. Rogers, R.D., Seddon, K.R., Eds. Ionic Liquids IIIB: Fundamentals, Progress, Challenges, and Opportunities-Transformations and Processes. ACS Symp. Ser.; American Chemical Society: Washington, D.C., USA, 2005; Volume 902.
2. Rogers, R.D., Seddon, K.R., Eds. Ionic Liquids IIIA: Fundamentals, Progress, Challenges, and Opportunities-Properties and Structure; ACS Symp. Ser.; American Chemical Society: Washington D.C., USA, 2005; Volume 901.
3. Wasserscheid, P.; Welton, T., Eds. Ionic Liquids in Synthesis, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2007.
4. Scammells, J.; Scott, J.L.; Singer, R.D. Ionic Liquids: the Neglected Issues. Aust. J. Chem. 2005, 58, 155-169.
5. Anderson, J.L.; Armstrong, D.W.; Wei, G.-T. Ionic Liquids in Analytical Chemistry. Anal. Chem. 2006, 78, 2892-2902.
6. Earle, J.; Seddon, K.R. Ionic Liquids. Green Solvents for the Future. Pure Appl. Chem. 2000, 72, 1391-1398.
7. Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis. Chem. Rev. 1999, 99, 2071-2084. (Pubitemid 129585179)
8. Endres, F.; El Abedin, S.Z. Air and water stable ionic liquids in physical chemistry. Phys. Chem. Chem. Phys. 2006, 8, 2101-2116.
9. van Rantwijk, F.; Lau, R.M.; Sheldon, R.A. Biocatalysis in Ionic Liquids. Trends Biotechnol. 2003, 21, 131-138.
10. Beletskaya, I.P.; Cheprakov, A.V. The Heck reaction as a sharpening stone of palladium catalysis. Chem. Rev. 2000, 100, 3009-3066.
11. Daves, G.D., Jr.; Hallberg, A. 1,2-Additions to heteroatom-substituted olefins by organopalladium reagents. Chem. Rev. 1989, 89, 1433-1445.
12. Trzeciak, A.M.; Ziòlkowski, J.J. The role of ionic liquids in palladium-catalyzed C-C bond-forming reactions. In Advances Organometallic Chemistry Research; Yamamoto, K., Ed.; Nova Science Publishers: NewYork, NY, USA, 2007; p. 177.
13. Liu, Y.; Wang, S.-S.; Liu, W.; Wan, Q.-X.; Wu, H.-H.; Gao, G.-H. Transition-metal catalyzed carbon-carbon couplings mediated with functionalized ionic liquids, supported-ionic liquid phase, or ionic liquid media. Curr. Org. Chem. 2009, 13, 1322-1346.
14. Oestreich, M. The Mizoroki-Heck Reaction; John Wiley & Sons: New York, USA, 2009.
15. Jeffery, T. Palladium-catalysed vinylation of organic halides under solid-liquid phase transfer conditions. J. Chem. Soc. Chem. Commun. 1984, 1287-1289.
16. Kaufmann, D.; Nouroozian, M.; Henze, H. Molten salts as an efficient medium for palladium catalyzed C-C coupling reactions. Synlett 1996, 1091-1092. (Pubitemid 126426967)
17. Slagt, V.F.; de Vries, A.H.M.; de Vries, J.G.; Kellogg R.M. Practical aspects of carbon?carbon cross-coupling reactions using heteroarenes. Org. Proc. Res. Devel. 2010, 14, 30-47.
18. Carmichael, A.J.; Earle, M.J.; Holbrey, J.D.; Mc Cormac, P.B.; Seddon, K.R. The Heck reaction in ionic liquids: A multiphasic catalyst system. Org. Lett. 1999, 1, 997-1000.
19. Schmidt, A.F.; Al Haleipa, A.; Smirnov, V.V. Interplays between reactions within and without the catalytic cycle of the Heck reaction as a clue to the optimization of the synthetic protocol. Synlett 2006, 2861-2878, and references cited therein.
20. Jeffery, T. On the efficiency of tetraalkylammonium salts in Heck type reactions. Tetrahedron 1996, 52, 10113-10130. (Pubitemid 26233623)
21. Herrmann, W.A.; Böhm, V.P.W. Heck reaction catalyzed by phospha-palladacycles in non-aqueous ionic liquids. J. Organomet. Chem. 1999, 572, 141-145.
22. Böhm, V.P.W.; Herrmann, W.A. Coordination chemistry and mechanisms of metal-catalyzed C-C coupling reactions, Part 12 Nonaqueous Ionic Liquids: Superior Reaction Media for the Catalytic Heck-Vinylation of Chloroarenes. Chem Eur. J. 2000, 6, 1017-1025.
23. 4NBr mixture as an efficient medium for the stereoselective synthesis of (E)- and (Z)-3,3-diarylacrylates. Synlett 2002, 439-442. (Pubitemid 34208280)
24. Bouquillon, S.; Gauchegui, B.; Estrine, B.; Hénin, F.; Muzart, J. Heck arylation of allylic alcohols in molten salts. J. Organomet. Chem. 2001, 634, 153-156. (Pubitemid 33646232)
25. Calò, V.; Nacci, A.; Monopoli, A. Effects of ionic liquids on Pd-catalysed carbon-carbon bond formation. Eur. J. Org. Chem. 2006, 3791-3802. (Pubitemid 33362218)
26. Calò, V.; Nacci, A.; Monopoli, A.; Laera, S.; Cioffi, N. Pd nanoparticles catalyzed stereospecific synthesis of β-aryl cinnamic esters in ionic liquids. J. Org. Chem. 2003, 68, 2929-2933. (Pubitemid 36519130)
27. Calò, V.; Nacci, A.; Monopoli, A.; Detomaso, A.; Iliade, P. Pd nanoparticle catalyzed Heck arylation of 1,2-disubstituted alkenes in ionic liquids. Study on factors affecting the regioselectivity of the coupling process. Organometallics 2003, 22, 4193-4197.
28. Calò, V.; Nacci, A.; Monopoli, A.; Cotugno, P. Heck ractions with palladium nanoparticles in ionic liquids: coupling of aryl chlorides with deactivated olefins. Angew. Chem. Int. Ed. 2009, 48, 6101-6103.
29. Xu, L.; Chen, W.; Xiao, J. Heck reaction in ionic liquids and the in situ identification of N-heterocyclic carbene complexes of palladium. Organometallics 2000, 19, 1123-1127.
30. Wu, X.; Mo, J.; Li, X.; Hyder, Z.; Xiao, J. Green chemistry: C-C coupling and asymmetric reduction by innovative catalysis. Prog. Nat. Sci. 2008, 18, 639-652.
31. Mo, J.; Xu, L.; Xiao, J. Ionic liquid promoted, highly regioselective Heck arylation of electron-rich olefins by aryl halides. J. Am. Chem. Soc. 2005, 127, 751-760. (Pubitemid 40174400)
32. Mo, J.; Xiao, J. The Heck reaction of electron-rich olefins with regiocontrol by hydrogen-bond donors. Angew. Chem. Int. Ed. 2006, 45, 4152-4157. (Pubitemid 44105672)
33. 2-catalyzed intramolecular Heck reaction. Tetrahedron Lett. 2004, 45, 6235-6237. (Pubitemid 39055801)
34. 6.Tetrahedron Lett. 2004, 45, 2775-2777. (Pubitemid 38317145)
35. Xiao, J.C; Twamley, B.; Shreeve, J.M. An ionic liquid-coordinated palladium complex: a highly efficient and recyclable catalyst for the Heck reaction. Org. Lett. 2004, 6, 3845-3847. (Pubitemid 39421959)
36. Wang, R.; Piekarski, M.P.; Shreeve, J. New types of pyrazolyl- functionalized 2-methylimidazolium-based ionic liquids and their palladium(II) complexes: highly efficient, recyclable catalysts for C-C coupling reactions. Org. Biomol. Chem. 2006, 4, 1878-1886.
37. Wang, R.; Zeng, Z.; Twamley, B.; Piekarski, M.M.; Shreeve, J. Synthesis and characterization of pyrazolyl-functionalized imidazolium-based ionic liquids and hemilabile palladium(II) carbene complex catalyzed Heck reaction. Eur. J. Org. Chem. 2007, 655-661.
38. Wang, R.; Twamley, B.; Shreeve, J. A highly efficient, recyclable catalyst for C-C coupling reactions in ionic liquids: pyrazolyl-functionalized N-heterocyclic carbene complex of palladium(II). J. Org. Chem. 2006, 71, 426-429. (Pubitemid 43128116)
39. Vergas, V.C.; Rubio, R.J.; Holis, T.K.; Salcido, M.E. Efficient route to 1,3-Di-N-imidazolylbenzene. A comparison of monodentate vs bidentate carbenes in Pd-catalyzed cross coupling. Org. Lett. 2003, 5, 4847-4849.
40. Jin, C.M.; Twamley, B.; Shreeve, J. Low-melting dialkyl- and bis(polyfluoroalkyl)-substituted 1,1'-methylene-bis(imidazolium) and 1,1'-methylenebis(1,2,4-triazolium) bis(trifluoromethanesulfonyl) amides: ionic liquids leading to bis(N-heterocyclic carbene) complexes of palladium. Organometallics 2005, 24, 3020-3023. (Pubitemid 40891232)
41. Wang, R.; Jin, C.M.; Twamley, B.; Shreeve, J. Syntheses and characterization of unsymmetric dicationic salts incorporating imidazolium and triazolium functionalities. Inorg. Chem. 2006, 45, 6396-6403.
42. 2) as a reusable reaction medium and PdII ligand in Heck reactions of aryl halides with styrene and n-butyl acrylate. Eur. J. Org. Chem. 2007, 2197-2201.
43. Zhao, D.; Fei,. Z.; Geldbach, T.J.; Scopelliti, R.; Dyson, P.J. Nitrile-functionalized pyridinium ionic liquids: synthesis, characterization, and their application in carbon-carbon coupling reactions. J. Am. Chem. Soc. 2004, 126, 15876-15882. (Pubitemid 39602445)
44. Chiappe, C.; Pieraccini, D.; Zhao, D.; Fei, Z.; Dyson, P.J. Remarkable anion and cation effects on Stille reactions in functionalised ionic liquids. Adv. Synth. Catal. 2006, 348, 68-74. (Pubitemid 43155977)
45. Fei, Z.; Zhao, D.; Pieraccini, D.; Ang, W.H.; Geldbach, T.J.; Scopelliti, R.; Chiappe, C.; Dyson, P.J. Development of nitrile-functionalized ionic liquids for C-C coupling reactions: implication of carbene and nanoparticle catalysts. Organometallics 2007, 26, 1588-1598. (Pubitemid 46549021)
46. Ye, C.; Xiao, J.C.; Twamley, B.; LaLonde, A.D.; Norton, M.G.; Shreeve, J.M. Basic ionic liquids: facile access for Carbon-Carbon bond formation reactions and ready access to palladium nanoparticles. Eur. J. Org. Chem. 2007, 5095-15011
47. Chiappe, C.; Melai, B.; Sanzone, A.; Valentini, G. Basic ionic liquids based on monoquaternized 1,4-diazobicyclo2.2.2octane (dabco) and dicyanamide anion: Physicochemical and solvent properties. Pure Appl. Chem. 2009, 81, 2035-2043.
48. Handy, S.T.; Okello, M.; Dickenson, G. Solvents from biorenewable sources: ionic liquids based on fructose. Org. Lett. 2003, 5, 2513-2515. (Pubitemid 37140897)
49. Bellina, F.; Bertoli, A.; Melai, B.; Scalesse, F.; Signori, F.; Chiappe, C. Synthesis and properties of glycerylimidazolium based ionic liquids: A promising class of task-specific ionic liquids. Green Chem. 2009, 11, 622-629.
50. Sheldon, R. Catalytic reactions in ionic liquids. Chem. Comm. 2001, 2399-2407. (Pubitemid 33124059)
51. Cai, Y.; Liu, Y. Efficient palladium-catalyzed Heck reactions mediated by diol-functionalized imidzolium ionic liquids. Cat. Comm. 2009, 10, 1390-1393.
52. Cai, Y.; Lu, Y.; Liu, Y.; Gao, G.H. Imidazolium ionic liquid-supported diol: an efficient and recyclable phosphine-free ligand for palladium catalyzed Heck reaction. Catal. Lett.2007, 119, 154-158. (Pubitemid 47609413)
53. Wang, L.; Li, H.; Li, P. Task-specific ionic liquid as base, ligand and reaction medium for the palladium-catalyzed Heck reaction. Tetrahedron 2008, 65, 364-368.
54. Wan, Q.X.; Liu, Y.; Lu, Y.; Li, M.; Wu, H.H. Palladium-catalyzed Heck reaction in the multi-functionalized ionic liquid compositions. Catal. Lett.2008, 121, 331-336.
55. Wan, Q.X.; Liu, Y.; Cai, Y.Q. A hybrid P,N-ligand functionalized imidazolium salt for palladium- catalyzed Heck reactions in ionic liquid solution. Catal. Lett. 2009, 127, 386-391.
56. Li, S.; Li, Y.; Xie, H.; Zhang, S.; Xu, J. Bronsted guanidine acid-base ionic liquids: novel reaction media for the palladium catalyzed Heck reaction. Org. Lett. 2006, 8, 391-394. (Pubitemid 43241668)
57. Hagiwara, H.; Shimizu, Y.; Hoshi, T.; Suzuki, T.; Ando, M.; Ohkubo, K.; Yokoyama, C. Heterogeneous Heck reaction catalyzed by Pd/C in ionic liquid. Tetrahedron Lett. 2001, 42, 4349-4351. (Pubitemid 32524139)
58. 2 in ionic liquid on silica: application to sustainable Mizoroki-Heck reaction. Org. Lett. 2004, 6, 2325-2328. (Pubitemid 38952531)
59. 2 immobilized on reversed phase silica gel with the aid of an ionic liquid. Chem. Comm. 2005, 2942-2944. (Pubitemid 40917043)
60. Okubo, K.; Shirai, M.; Yokoyama, C. Heck reactions in non-aqueous ionic liquid using silica supported palladium complex catalysts. Tetrahedron Lett. 2002, 43, 7115-7118. (Pubitemid 35246121)
61. Aslanov, L.A.; Kabachii, Y.A.; Kochev, S.Yu.; Romanovsky, B.V.; Valetsky, P.M.; Volkov, V.V.; Yatsenko, A.V.; Zakharov, V.N. Mesoporous soot-supported palladium as a heterogeneous catalyst for the Heck reaction in ionic liquids. Mendeleev Commun. 2008, 18, 334-335.
62. Safavi, A.; Maleki, N.; Iranpoor, N.; Firouzabadi, H.; Banazadeh, A.R.; Azadi, R.; Sedaghati, F. Highly efficient and stable palladium nanocatalysts on an ionic liquid-modified xerogel. Chem. Commun. 2008, 6155-6157.
63. 2 catalyst in an ionic liquid phase confined in silica gels. Application to Heck-Mizoroki reaction. New J. Chem. 2009, 33, 2015-2021.
64. Calò, V.; Nacci, A.; Monopoli, A.; Fornaro, A.; Sabbatini, L.; Cioffi, N.; Ditaranto, N. Heck reaction catalyzed by nanosized palladium on chitosan in ionic liquid. Organometallics 2004, 23, 5154-5158.
65. Ma, X.; Zhou, Y.; Zhang, J.; Zhu, A.; Jiang, T.; Han, B. Solvent-free Heck reaction catalyzed by a recyclable Pd catalyst supported on SBA-15 via an ionic liquid. Green Chem. 2008, 10, 59-66.
66. Zhao, D.; Fei, Z.; Ang, W.H.; Dyson, P.J. A strategy for the synthesis of transition-metal nanoparticles and their transfer between liquid phases. Small 2006, 2, 879-883. (Pubitemid 43892239)
67. Yang, X.; Fei, Z.; Zhao, D.; Hang, W.H.; Li, Y.; Dyson, P.J. Palladium nanoparticles stabilized by an ionic polymer and ionic liquid: A versatile system for C-C cross-coupling reactions. Inorg. Chem. 2008, 47, 3292-3297.
68. Mehnert, C.P.; Cook, R.A.; Dispenziere, N.C.; Afeworki, A. Supported Ionic Liquid Catalysis - A New Concept for Homogeneous Hydroformylation Catalysis. J. Am. Chem. Soc. 2002, 124, 12932-12933. (Pubitemid 35247089)
69. Hagiwara, H.; Ko, K.H.; Hoshi, T.; Suzuki, T. Supported ionic liquid catalyst (Pd-SILC) for highly efficient and recyclable Suzuki-Miyaura reaction. Chem. Commun. 2007, 2838-2840. (Pubitemid 47035558)
70. Wan, L.; Zhang, Y.; Xie, C.; Wang, Y. PEG-supported imidazolium chloride: a highly efficient and reusable reaction medium for the Heck reaction. Synlett 2005, 12, 1861-1864. (Pubitemid 41133105)
71. Reetz, M.T.; Westermann, E. Phosphane-free palladium-catalyzed coupling reactions: the decisive role of Pd nanoparticles. Angew. Chem. Int. Ed. 2000, 39, 165-168. (Pubitemid 30265703)
72. Cassol, C.C.; Umpierre, A.P.; Machado, G.; Wolke, S.I.; Dupont, J. The role of Pd nanoparticles in ionic liquid in the Heck reaction. J. Am. Chem. Soc. 2005, 127, 3298-3299. (Pubitemid 40365267)
73. Astruc, D.; Lu, F.; Aranzaes, J.R. Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 2005, 44, 7852-7872. (Pubitemid 41818885)
74. Slagt, V.F.; de Vries, A.H.M.; de Vries, J.G.; Kellogg, R.M. Practical aspects of carbon-carbon cross-coupling reactions using heteroarenes. Org. Proc. Res. Devel. 2010, 14, 30-47.
75. Pryjomska-Ray, I.; Trzeciak, A.M.; Ziòlkowski, J.J.Z. Base-free efficient palladium catalyst of Heck reaction in molten tetrabutylammonium bromide. J. Mol. Catal. A 2006, 257, 3-8. (Pubitemid 44332302)
76. Arduengo, III, A.J.; Harlow, R.L.; Klim, M. A stable crystalline carbene. J. Am. Chem. Soc. 1991, 113, 361-363.
77. Nolan, S.P. N-Heterocyclic Carbenes in Synthesis; Wiley- VCH: Weinheim, Germany, 2006.
78. Glorius, F. N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer-Verlag: Berlin, Germany, 2007.
79. Handy, S.T.; Okello, M. The 2 Position of Imidazolium Ionic Liquids: Substitution and Exchange. J. Org. Chem. 2005, 70, 1915-1918. (Pubitemid 40300160)
80. Gayet, F.; Marty, J.-D.; Lauth-de Viguerie, N. Palladate Salts from Ionic Liquids as Catalysts in the Heck Reaction. ARKIVOC 2008, 61-76.
81. Von Schenck, H.; Akermark, B.; Svenson, M. Electronic Control of the Regiochemistry in the Heck Reaction. J. Am. Chem. Soc. 2003, 125, 3503-3508. (Pubitemid 36512424)
82. Deeth, R.J.; Smith, A.; Brown, J.M. Electronic control of the regiochemistry in palladium-phosphine catalyzed intermolecular Heck reactions. J. Am. Chem. Soc. 2004, 126, 7144-7151. (Pubitemid 38855414)
83. Cabri, W.; Candiani, I. Recent Developments and New Perspectives in the Heck Reaction. Acc. Chem. Res. 1995, 28, 2-7.
84. Xu, L.; Chen, W.; Ross, J.; Xiao, J. Palladium-Catalyzed Regioselective Arylation of an Electron-Rich Olefin by Aryl Halides in Ionic Liquids. Org. Lett. 2001, 3, 295-297. (Pubitemid 33629390)
85. McConville, M.; Saidi, O.; Blacker, J.; Xiao, J. Regioselective Heck vinylation of electron-rich olefins with vinyl halides: is the neutral pathway in operation? J. Org. Chem. 2009, 74, 2692-2698; and references cited herein.
86. Amatore, C.; Godin, B.; Jutand, A.; Lamaitre, F. Rate and Mechanism of the Reaction of Aryl-Palladium Complexes ligated by a bidentate P,P ligand with an Electron-Rich Alkene (Isobutylvinyl Ether) in Heck Reactions. Organometallics 2007, 26, 1757-1761. (Pubitemid 46549039)
87. Amatore, C.; Godin, B.; Jutand, A.; Lemaitre, F. Rate and Mechanism of the Reaction of Alkenes with Aryl-Palladium Complexes ligated by a bidentate P,P ligand in Heck reactions. Chem. Eur. J. 2007, 13, 2002-2011. (Pubitemid 46941906)
88. Calò, V.; Nacci, A.; Monopoli, A.; Ferola, V. Palladium-Catalyzed Heck Arylations of Allyl Alcohols in Ionic Liquids: Remarkable Base Effect on the Selectivity. J. Org. Chem. 2007, 72, 2596-12061 (Pubitemid 46536191)