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d-Glucosamine as an efficient and green additive for palladium-catalyzed Heck reaction

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The Heck coupling of haloarenes with various alkenes was successfully performed in the presence of 0.5 mole % Pd(OAc)2 and 1.0 mole % d-glucosamine as an additive with K2CO3 as the optimal base in a mixture of H2O/iPrOH (φ r = 2: 1) as the reaction solvent at 80°C after 6 h. d-Glucosamine was found to be an inexpensive, air-stable, easy to available, and efficient additive in palladium-catalyzed Heck reactions of aryl iodides (67–95 % conversion) and bromides (38–72 % conversion).

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  • Allam, B. K., & Singh, K. N. (2011). An efficient phosphinefree Heck reaction in water using Pd(L-proline)2 as the catalyst under microwave irradiation. Synthesis, 2011, 1125–1131. DOI: 10.1055/s-0030-1258452.

    Article  Google Scholar 

  • Amini, M., Bagherzadeh, M., Moradi-Shoeili, Z., & Boghaei, D. M. (2012). Pd(OAc)2 without added ligand as an active catalyst for Mizoroki-Heck reaction in aqueous media. RSC Advances, 2, 12091–12095. DOI: 10.1039/c2ra21459h.

    Article  CAS  Google Scholar 

  • Andersen, N. G., & Keay, B. A. (2001). 2-Furyl phosphines as ligands for transition-metal-mediated organic synthesis. Chemical Reviews, 101, 997–1030. DOI: 10.1021/cr000024o.

    Article  CAS  Google Scholar 

  • Bagherzadeh, M., Amini, M., Ellern, A., & Woo, L. K. (2012). Palladium and copper complexes with oxygen-nitrogen mixed donors as efficient catalysts for the Heck reaction. Inorganica Chimica Acta, 383, 46–51. DOI: 10.1016/j.ica.2011.10.040.

    Article  CAS  Google Scholar 

  • Bradshaw, M., Zou, J. L., Byrne, L., Iyer, K. S., Stewart, S. G., & Raston, C. L. (2011). Pd(II) conjugated chitosan nanofibre mats for application in Heck cross-coupling reactions. Chemical Communications, 47, 12292–12294. DOI: 10.1039/c1cc14717j.

    Article  CAS  Google Scholar 

  • Bräse, S., & de Meijere, A. (1998). Palladium-catalyzed coupling of organyl halieds to alkenes — the Heck reaction. In F. Diederich, & P. J. Stang (Eds.), Metal-catalyzed crosscoupling reactions (pp. 99–166). Weinheim, Germany: Wiley-VCH.

    Google Scholar 

  • Cornils, B., & Herrmann, W. A. (1998). Aqueous phase organometallic chemistry: Concepts and applications. Weinheim, Germany: Wiley-VCH.

    Google Scholar 

  • Diéguez, M., Claver, C., & Pàmies, O. (2007). Recent progress in asymmetric catalysis using chiral carbohydrate-based ligands. European Journal of Organic Chemistry, 2007, 4621–4634. DOI: 10.1002/ejoc.200700082.

    Article  Google Scholar 

  • Genet, J. P., & Savignac, M. (1999). Recent developments of palladium(0) catalyzed reactions in aqueous medium. Journal of Organometallic Chemistry, 576, 305–317. DOI: 10.1016/s0022-328x(98)01088-2.

    Article  Google Scholar 

  • Grasa, G. A., Singh, R., Stevens, E. D., & Nolan, S. P. (2003). Catalytic activity of Pd(II) and Pd(II)/DAB-R systems for the Heck arylation of olefins. Journal of Organometallic Chemistry, 687, 269–279. DOI: 10.1016/s0022-328x(03)00375-9.

    Article  CAS  Google Scholar 

  • Grieco, P. A. (1998). Organic synthesis in water. London, UK: Thomson Science.

    Book  Google Scholar 

  • Heck, R. F. (1987) Palladium reagents in organic synthesis: Best synthetic methods. London, UK: Academic Press.

    Google Scholar 

  • Iranpoor, N., Firouzabadi, H., Tarassoli, A., & Fereidoonnezhad, M. (2010). 1,3,2,4-Diazadiphosphetidines as new P-N ligands for palladium-catalyzed Heck reaction in water. Tetrahedron, 66, 2415–2421. DOI: 10.1016/j.tet.2010.01.099.

    Article  CAS  Google Scholar 

  • Li, C. H., & Chan, T. H. (1997). Organic reactions in aqueous media. New York, NY, USA: Wiley.

    Google Scholar 

  • Makhubela, B. C. E., Jardine, A., & Smith, G. S. (2011). Pd nanosized particles supported on chitosan and 6-deoxy-6-amino chitosan as recyclable catalysts for Suzuki-Miyaura and Heck cross-coupling reactions. Applied Catalysis A: General, 393, 231–241. DOI: 10.1016/j.apcata.2010.12.002.

    Article  CAS  Google Scholar 

  • Martin, R., & Buchwald, S. L. (2008). Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands. Accounts of Chemical Research, 41, 1461–1473. DOI: 10.1021/ar800036s.

    Article  CAS  Google Scholar 

  • Monopoli, A., Calò, V., Ciminale, F., Cotugno, P., Angelici, C., Cioffi, N., & Nacci, A. (2010). Glucose as a clean and renewable reductant in the Pd-nanoparticle-catalyzed reductive homocoupling of bromo- and chloroarenes in water. Journal of Organic Chemistry, 75, 3908–3911. DOI: 10.1021/jo1005729.

    Article  CAS  Google Scholar 

  • Phan, N. T. S., Sluys, M. V. D., & Jones, C. W. (2006). On the nature of the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings-homogeneous or heterogeneous catalysis, a critical review. Advanced Synthesis & Catalysis, 348, 609–679. DOI: 10.1002/adsc.200505473.

    Article  CAS  Google Scholar 

  • Thakur, K. G., Ganapathy, D., & Sekar, G. (2011). d-Glucosamine as a green ligand for copper catalyzed synthesis of primary aryl amines from aryl halides and ammonia. Chemical Communications, 47, 5076–5078. DOI: 10.1039/c1cc10568j.

    Article  CAS  Google Scholar 

  • Wolfson, A., & Dlugy, C. (2007). Palladium-catalyzed Heck and Suzuki coupling in glycerol. Chemical Papers, 61, 228–232. DOI: 10.2478/s11696-007-0026-3.

    Article  CAS  Google Scholar 

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Correspondence to Mojtaba Amini.

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Amini, M., Etemadi, H. d-Glucosamine as an efficient and green additive for palladium-catalyzed Heck reaction. Chem. Pap. 67, 759–763 (2013).

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