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Palladium supported on silica gel confined ionic liquid as a reusable catalyst for carbon–carbon cross coupling reaction in water

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Abstract

We have developed an efficient method for carbon–carbon cross coupling reactions using a palladium-catalyst supported on porous silica gel confined ionic liquid, 1-decyl-3-methyl imidazolium fluoroborate ([dmim]BF4) in water at 80 °C. A variety of substituted aryl bromides underwent Suzuki and Heck coupling with various boronic acids and acrylates respectively to produce a series of functionalized biaryls and cinnamates in high yields. The catalyst is stable, recyclable and it offers very high turnover numbers.

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References

  • Beletskaya IP, Cheprakov AV (2000) The Heck reaction as a sharpening stone of palladium catalysis. Chem Rev 100:3009–3066

    Article  CAS  Google Scholar 

  • Chinchilla R, Najera C (2007) The Sonogashira reaction: a booming methodology in synthetic organic chemistry. Chem Rev 107:874–922

    Article  CAS  Google Scholar 

  • Dupont J, de Souza RF, Suarez PAZ (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 102:3667–3692

    Article  CAS  Google Scholar 

  • Espinet P, Echavarren AM (2004) The mechanisms of the Stille reaction. Angew Chem Int Ed 43:4704–4734

    CAS  Google Scholar 

  • Hagiwara H, Ko KH, Hoshi T, Suzuki T (2007) Supported ionic liquid catalyst (Pd-SILC) for highly efficient and recyclable Suzuki–Miyaura reaction. Chem Commun 43:2838–2840

    Article  Google Scholar 

  • Hagiwara H, Nakamura T, Hoshi T, Suzuki T (2011) Palladium-supported ionic liquid catalyst (Pd-SH-SILC) immobilized on mercapto propyl silica gel as a chemoselective, reusable and heterogeneous catalyst for catalytic hydrogenation. Green Chem 13:1133–1137

    Article  CAS  Google Scholar 

  • Hatanaka Y, Hiyama T (1988) Cross-coupling of organosilanes with organic halides mediated by palladium catalyst and tris(diethy1amino)sulfonium difluorotrimethylsilicate. J Org Chem 53:918–920

    Article  CAS  Google Scholar 

  • Heck RF, Nolley JP Jr (1972) Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J Org Chem 37:2320–2322

    Article  CAS  Google Scholar 

  • Hiyama T (2002) How I came across the silicon-based cross-coupling reaction. J Org Met Chem 653:58–61

    Article  CAS  Google Scholar 

  • Li D, Shi F, Guo S, Deng Y (2004) One-pot synthesis of silica gel confined functional ionic liquids: effective catalysts for deoximation under mild conditions. Tetrahedron Lett 45:265–268

    Article  CAS  Google Scholar 

  • Miyaura N, Suzuki A (1995) Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 95:2457–2483

    Article  CAS  Google Scholar 

  • Shi F, Zhang Q, Li D, Deng Y (2005a) Silica-gel confined ionic liquids: a new attempt for the development of supported nanoliquid catalysis. Chem Eur J 11:5279–5288

    Article  CAS  Google Scholar 

  • Shi F, Zhang Q, Gu Y, Deng Y (2005b) Silica gel confined ionic liquid+metal complexes for oxygen-free carbonylation of amines and nitrobenzene to ureas. Adv Synth Catal 347:225–230

    Article  CAS  Google Scholar 

  • Sonogashira K, Tohda Y, Hagihara N (1975) A convenient synthesis of acetylenes: catalytic substitution of acetylenic hydrogen with bromoalkenes, iodoarenes, and bromopyridines. Tetrahedron Lett 50:4467–4470

    Article  Google Scholar 

  • Stille JK (1986) The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew Chem Int Ed 25:508–524

    Article  Google Scholar 

  • Suzuki A (1999) Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998. J Org Met Chem 576:147–168

    Article  CAS  Google Scholar 

  • Tsuji J (1969) Carbon-carbon bond formation via palladium complexes. Acc Chem Res 2:144–152

    Article  CAS  Google Scholar 

  • Virtanen P, Karhu H, Kordas K, Mikkola JP (2007) The effect of ionic liquid in supported ionic liquid catalysts (SILCA) in the hydrogenation of α, β-unsaturated aldehydes. Chem Eng Sci 62:3660–3671

    Article  CAS  Google Scholar 

  • Volland S, Gruit M, Regnier T, Viau L, Lavastre O, Vioux A (2009) Encapsulation of Pd(OAc)2 catalyst in an ionic liquid phase confined in silica gels. Application to Heck–Mizoroki reaction. New J Chem 33:2015–2021

    Article  CAS  Google Scholar 

  • Wasserscheid P, Keim W (2000) Ionic liquids—new solutions for transition metal catalysis. Angew Chem Int Ed 39:3772–3789

    Article  CAS  Google Scholar 

  • Welton T (1999) Room temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071–2084

    Article  CAS  Google Scholar 

  • Yin L, Leibescher J (2007) Carbon-carbon coupling reactions catalysed by heterogeneous palladium catalysts. Chem Rev 107:133–173

    Article  CAS  Google Scholar 

Download references

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Correspondence to Brindaban C. Ranu.

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Ghosh, S., Dey, R., Ahammed, S. et al. Palladium supported on silica gel confined ionic liquid as a reusable catalyst for carbon–carbon cross coupling reaction in water. Clean Techn Environ Policy 16, 1767–1771 (2014). https://doi.org/10.1007/s10098-013-0658-7

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  • DOI: https://doi.org/10.1007/s10098-013-0658-7

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