Synlett 2016; 27(08): 1193-1201
DOI: 10.1055/s-0035-1561286
cluster
© Georg Thieme Verlag Stuttgart · New York

Gold Nanoparticles Supported on Polyacrylamide Containing a Phosphorus Ligand as an Efficient Heterogeneous Catalyst for Three-Component Synthesis of Propargylamines in Water

Mohammad Gholinejad*
a  Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P. O. Box 45195-1159, Gavazang, Zanjan 45137-6731, Iran   Email: gholinejad@iasbs.ac.ir
,
Fatemeh Hamed
a  Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P. O. Box 45195-1159, Gavazang, Zanjan 45137-6731, Iran   Email: gholinejad@iasbs.ac.ir
,
Carmen Nájera*
b  Departamento de Química Orgánica and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain   Email: cnajera@ua.es
› Author Affiliations
Further Information

Publication History

Received: 23 September 2015

Accepted after revision: 18 November 2015

Publication Date:
28 December 2015 (online)


Abstract

Gold nanoparticles supported on a polyacrylamide containing a phosphinite ligand have been synthesized and characterized using different techniques such as TEM, SEM, EDX, XPS, and solid UV analyses. The new material was successfully applied as a heterogeneous catalyst for the three-component A3 coupling of amines, aldehydes, and alkynes to give propargylamines. Reactions are performed in neat water at 80 °C with only 0.05 mol% catalyst loading. The heterogeneous catalyst is recyclable during seven consecutive runs with small decrease in activity.

Supporting Information

 
  • References and Notes

  • 1 Soderberg BC. G. Coord. Chem. Rev. 2003; 241: 147
    • 2a Li Z, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
    • 2b Hashmi AS. K. Chem. Rev. 2007; 107: 3180
    • 3a Tsunoyama H, Sakurai H, Negishi Y, Tsukuda T. J. Am. Chem. Soc. 2005; 127: 9374
    • 3b Guan B, Xing D, Cai G, Wan X, Yu N, Fang Z, Yang L, Shi Z. J. Am. Chem. Soc. 2005; 127: 18004
    • 3c Enache DI, Edwards JK, Landon P, Solsona-Espriu B, Carley AF, Herzing AA, Watanabe M, Kiely CJ, Knight DW, Hutchings GJ. Science 2006; 311: 362
    • 3d Miyamura H, Matsubara R, Miyazaki Y, Kobayashi S. Angew. Chem. Int. Ed. 2007; 46: 4151
    • 3e Rautiainen S, Simakova O, Guo H, Leino A.-R, Kordás K, Murzin D, Leskelä M, Repo T. Appl. Catal., A 2014; 485: 202
    • 3f Li L, Dou L, Zhang H. Nanoscale 2014; 6: 3753
    • 3g Adnan RH, Andersson GG, Polson MI. J, Methad GF, Golovko VB. Catal. Sci. Technol. 2015; 5: 1323
    • 3h de Moura EM, Garcia MA. S, Gonçalves RV, Kiyohara PK, Jardim RF, Rossi LM. RSC Adv. 2015; 5: 15035
    • 3i Kokate M, Dapurkar S, Garadkar K, Gole A. J. Phys. Chem. C 2015; 119: 14214
  • 4 Bond GC, Thompson DT. Gold Bull. (Berlin, Ger.) 2000; 32: 41
  • 5 Comas-Vives A, Ujaque G. J. Am. Chem. Soc. 2013; 135: 1295
    • 6a Martín-Rodríguez M, Nájera C, Sansano JM, Wu F.-L. Tetrahedron: Asymmetry 2010; 21: 1184
    • 6b Martín-Rodríguez M, Nájera C, Sansano JM, de Cózar A, Cossío FP. Chem. Eur. J. 2011; 17: 14224
    • 6c López F, Mascareñas JL. Beilstein J. Org. Chem. 2011; 7: 1075
    • 6d Martín-Rodríguez M, Castelló LM, Nájera C, Sansano JM, Larrañaga O, de Cózar A, Cossío FP. Beilstein J. Org. Chem. 2013; 9: 2422
  • 7 Corma A, Leyva-Pérez A, Sabater MJ. Chem. Rev. 2011; 111: 1657
    • 8a Brooner RE. M, Robertson BD, Widenhoefer RA. Organometallics 2014; 33: 6466
    • 8b Speck K, Karaghiosoff K, Magauer T. Org. Lett. 2015; 17: 1982
    • 9a Mitsudome T, Noujima A, Mikami Y, Mizugaki T, Jitsukawa K, Kaneda K. Chem. Eur. J. 2010; 16: 11818
    • 9b Ni J, He L, Liu Y.-M, Cao Y, He H.-Y, Fan K.-N. Chem. Commun. 2011; 47: 812
    • 10a Gonzalez-Arellano C, Abad A, Corma A, García H, Iglesias M, Sánchez F. Angew. Chem. Int. Ed. 2007; 46: 1536
    • 10b Li P, Wang L, Wang M, You F. Eur. J. Org. Chem. 2008; 5946
    • 10c Beaumont SK, Kyriakou G, Lambert RM. J. Am. Chem. Soc. 2010; 132: 12246
    • 10d Corma A, Juarez R, Boronat M, Sánchez F, Iglesias M, García H. Chem. Commun. 2011; 47: 1446
    • 10e Li G, Jiang D.-E, Liu C, Yu C, Jin R. J. Catal. 2013; 306: 177
    • 10f Sisodiya S, Wallenberg LR, Lewin E, Wendt OF. Appl. Catal., A 2015; 503: 69
    • 11a González-Arellano C, Corma A, Iglesias M, Sánchez F. J. Catal. 2006; 238: 497
    • 11b Han J, Liu Y, Guo R. J. Am. Chem. Soc. 2009; 131: 2060
    • 11c Hoshiya N, Shuto S, Arisawa M. Adv. Synth. Catal. 2011; 353: 743
    • 11d Shah D, Kaur H. J. Mol. Catal. A: Chem. 2014; 381: 70
    • 11e Dumbre DK, Yadav PN, Bhargava SK, Choudhary VR. J. Catal. 2015; 301: 134
  • 12 Skouta R, Li C.-J. Tetrahedron 2008; 64: 4917
  • 13 Zani L, Bolm C. Chem. Commun. 2006; 4263
  • 14 Wei C, Lee CJ. J. Am. Chem. Soc. 2003; 125: 9584
    • 15a Price GA, Brisdon AK, Flower KR, Pritchard RG, Quayle P. Tetrahedron Lett. 2014; 55: 151
    • 15b Lo VK.-Y, Liu Y, Wong M, Che C.-M. Org. Lett. 2006; 8: 1529
    • 15c Yadav JS, Subba Reddy BV, Yadav NN, Gupta MK, Sridhar B. J. Org. Chem. 2008; 73: 6857
    • 15d Lo VK.-Y, Kung KK.-Y, Wong M.-K, Che C.-M. J. Organomet. Chem. 2009; 694: 583
    • 15e Elie BT, Levine C, Ubarretx-Belandia I, Varela-Ramírez A, Aguilera RJ, Ovalle R, Contel M. Eur. J. Inorg. Chem. 2009; 3421
    • 15f Zhang Q, Cheng M, Hu X, Li B.-G, Ji J.-X. J. Am. Chem. Soc. 2010; 132: 725
    • 15g Suzuki Y, Naoe S, Oishi S, Fujii N, Ohno H. Org. Lett. 2012; 14: 326
    • 15h Li J, Liu L, Ding D, Sun J, Ji Y, Dong J. Org. Lett. 2013; 15: 2884
    • 15i Bibek Jyoti BB, Jyoti S, Kumar DD. J. Nanosci. Nanotechnol. 2013; 13: 5080
    • 15j Srinivas V, Koketsu M. Tetrahedron 2013; 69: 8025
    • 15k Li J, Wang H, Sun J, Yang Y, Liu L. Org. Biomol. Chem. 2014; 12: 2523
    • 16a Kantam ML, Prakash BV, Reddy CR. V, Sreedhar B. Synlett 2005; 2329
    • 16b Zhang X, Corma A. Angew. Chem. Int. Ed. 2008; 47: 4358
    • 16c Datta KK. R, Reddy BV. S, Ariga K, Vinu A. Angew. Chem. Int. Ed. 2010; 49: 5961
    • 16d Abahmane L, Köhler JM, Groß GA. Chem. Eur. J. 2011; 17: 3005
    • 16e Villaverde G, Corma A, Iglesias M, Sánchez F. ACS Catal. 2012; 2: 399
    • 16f Bobadilla LF, Blasco T, Odriozola JA. Phys. Chem. Chem. Phys. 2013; 15: 16927
    • 16g Lili L, Xin Z, Shumin R, Ying Y, Xiaoping D, Jinsen G, Chunming X, Jing H. RSC Adv. 2014; 4: 13093
    • 16h Movahed SK, Lehi NF, Dabiri M. RSC Adv. 2014; 4: 42155
    • 16i Berrichi A, Bachir R, Benabdallah M, Choukchou-Braham N. Tetrahedron Lett. 2015; 56: 1302
    • 17a Ofir Y, Samanta B, Rotello VM. Chem. Soc. Rev. 2008; 37: 1814
    • 17b Navalón S, Álvaro M, García H. ChemCatChem 2013; 5: 3460
    • 18a Miyazaki Y, Kobayashi S. J. Comb. Chem. 2008; 10: 355
    • 18b Han J, Liu Y, Guo R. Adv. Funct. Mater. 2009; 19: 1112
    • 18c Murugan E, Rangasamy R. J. Polym. Sci., Part A: Polym. Chem. 2010; 48: 2525
    • 18d Burguete MI, García-Verdugo E, Luis SV, Restrepo JA. Phys. Chem. Chem. Phys. 2011; 13: 14831
    • 19a Sánchez JM, Hidalgo M, Salvadó V. React. Funct. Polym. 2001; 49: 215
    • 19b Giner X, Nájera C. Org. Lett. 2008; 10: 2919
    • 19c Schröder F, Tugny C, Salanouve E, Clavier H, Giordano L, Moraleda D, Gimbert Y, Mouriès-Mansuy V, Goddard JP, Fensterbank L. Organometallics 2014; 33: 4051
    • 19d Wan X.-K, Yuan S.-F, Lin Z.-W, Wang Q.-M. Angew. Chem. Int. Ed. 2014; 53: 2923
    • 19e Sarcher C, Farsadpour S, Taghizadeh Ghoochany L, Sun Y, Thiel WR, Roesky PW. Dalton Trans. 2014; 43: 2397
  • 20 Gholinejad M, Hamed F, Biji P. Dalton Trans. 2015; 44: 14293
    • 21a Karimi B, Gholinejad M, Khorasani M. Chem. Commun. 2012; 48: 8961
    • 21b Gholinejad M, Karimi B, Aminianfar A, Khorasani M. ChemPlusChem 2015; 80: 1573
  • 22 Hudson ZD, Sanghvi CD, Rhine MA, Ng JJ, Bunge SD, Hardcastle KI, Saadein MR, MacBeth CE, Eichler JF. Dalton Trans. 2009; 7473
  • 23 Mézailles N, Avarvari N, Maigrot N, Ricard L, Mathey F, Le Floch P, Cataldo L, Berclaz T, Geoffroy M. Angew. Chem. Int. Ed. 1999; 38: 3194
  • 24 Liu Y, Liu B, Wang Q, Liu Y, Li C, Hu W, Jing P, Zhao W, Zhang J. RSC Adv. 2014; 4: 5975
  • 25 A mixture of benzaldehyde (0.100 mL, 1 mmol), piperidine (0.160 mL, 1.5 mmol), phenylacetylene (0.165 mL, 1.5 mmol), catalyst (5 mg containing 0.05 mol% Au), and H2O (2 mL) was stirred at 80 °C for 1 d. The reaction mixture was cold down to r.t. and then extracted with EtOAc (3 × 10 mL). The organic phase was dried over anhydrous Na2SO4 and the solvent evaporated. The resulting propargylamine was purified by column chromatography on silica gel using EtOAc and hexane giving 270 mg (98% yield) of the pure product 1-(1,3-diphenylprop-2-yn-1-yl)piperidine.26 1H NMR (400 MHz, CDCl3): δ = 7.57–7.71 (m, 2 H), 7.55–7.56 (m, 2 H), 7.30–7.43 (m, 6 H), 4.90 (s, 1 H), 2.65 (br s, 4 H), 1.64–1.67 (m, 4 H), 1.48–1.51 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 138.2, 131.8, 128.7, 128.3, 128.2, 128.1, 127.7, 123.2, 88.2, 85.7, 62.4, 50.7, 25.9, 24.3.
    • 26a Lamblin M, Nassar-Hardy L, Hierso J.-C, Fouquet E, Felpin F.-X. Adv. Synth. Catal. 2010; 352: 33
    • 26b Widegren JA, Finke RG. J. Mol. Catal. A: Chem. 2003; 198: 317
  • 27 Shi L, Tu Y.-Q, Wang M, Zhang F.-M, Fan C.-A. Org. Lett. 2004; 6: 1001