Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2013; 45(9): 1201-1206
DOI: 10.1055/s-0033-1338293
DOI: 10.1055/s-0033-1338293
paper
PVC-Supported Palladium Nanoparticles: An Efficient Catalyst for Suzuki Cross-Coupling Reactions at Room Temperature
Authors
Further Information
Publication History
Received: 08 December 2012
Accepted after revision: 08 March 2013
Publication Date:
21 March 2013 (online)
Abstract
A simple and efficient protocol is described for a Suzuki reaction catalyzed by poly(vinyl chloride)-supported nanoparticles of metallic palladium at room temperature. Aryl iodides, bromides, and chlorides underwent smooth Suzuki reactions in aqueous ethanol, an environmentally friendly solvent, under ligand-free conditions to give good yields of the desired biaryl products. The heterogeneous catalyst could be used up to four times with no detectable metal leaching or loss of catalytic efficiency.
Key words
coupling reactions - supported catalysis - palladium - halides - biaryls - Suzuki reactionsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
Included are TEM and histogram data for PVC-Pd(0) and 1H and 13C NMR spectra and HRMS spectra for selected compounds.
- Supporting Information (PDF)
-
References
- 1a Handbook of Organopalladium Chemistry for Organic Synthesis. Negishi E, de Meijere A. Wiley; New York: 2002
- 1b Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 2a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
Reference Ris Wihthout Link
- 2b Kohei T, Miyaura N. Top. Curr. Chem. 2000; 219: 1
- 2c Partyka DV. Chem. Rev. 2011; 111: 1529
- 2d Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1978; 3437
- 3a Yang J, Liu S, Zheng J.-F, Zhou J. Eur. J. Org. Chem. 2012; 6248
- 3b Glasnov TN, Kappe CO. Adv. Synth. Catal. 2010; 352: 3089
- 4a Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
- 4b Climent MJ, Corma A, Iborre S. Chem. Rev. 2011; 111: 1072
- 5a Roucoux A, Schultz J, Patin H. Chem. Rev. 2002; 102: 3757
- 5b Daniel M.-C, Astruc D. Chem. Rev. 2004; 104: 293
- 5c Baca AJ, Ahn J.-H, Sun Y, Meitl MA, Menard E, Kim H.-S, Choi WM, Kim D.-H, Huang Y, Rogers JA. Angew. Chem. Int. Ed. 2008; 47: 5524
- 6 Astruc D, Lu F, Ruiz Aranzaes J. Angew. Chem. 2005; 117: 8062
- 7a Crooks RM, Zhao M, Sun L, Chechik V, Yeung LK. Acc. Chem. Res. 2001; 34: 181
- 7b Prastaro A, Ceci P, Chiancone E, Boffi A, Cirilli R, Colone RM, Fabrizi G, Stringaro A, Cacchi S. Green Chem. 2009; 11: 1929
- 7c Son SU, Jang Y, Yoon KY, Kang E, Hyeon T. Nano Lett. 2004; 4: 1147
- 7d Zhang Z, Wang Z. J. Org. Chem. 2006; 71: 7485
- 7e Yan N, Zhang J.-g, Tong Y, Yao S, Xiao C, Li Z, Kou Y. Chem. Commun. (Cambridge) 2009; 4423
- 7f Hu Y, Yu Y, Hou Z, Li H, Zhao X, Feng B. Adv. Synth. Catal. 2008; 350: 2077
- 8 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
Reference Ris Wihthout Link
- 9a Favier I, Madec D, Teuma E , Gómez Curr. Org. Chem. 2011; 15: 3127
- 9b Astruc D. Inorg. Chem. 2007; 46: 1884
- 9c Kumar VK. R, Sreedevi K, Gopidas KR. Eur. J. Org. Chem. 2012; 3447
- 10 Reetz MT, Westermann EA. Angew. Chem. 2000; 39: 165
- 11 Das P, Sharma D, Shil AK, Kumari A. Tetrahedron Lett. 2011; 52: 1176
- 12 Li Y, Hong XM, Collard DM, El-Sayed MA. Org. Lett. 2000; 2: 2385
- 13 Magdesieva TV, Nikitin OM, Levitsky OA, Zinovyeva VA, Bezverkhyy I, Zolotykhina EV, Vorotyntsev MA. J. Mol. Catal. A: Chem. 2012; 353–354: 50
- 14 Iranpoor N, Firouzabadi H, Motevalli S, Talebi M. J. Organomet. Chem. 2012; 707–709: 118
- 15 Huang X.-J, Dong F, Chen L, Li Y.-Q. Monatsh. Chem. 2008; 139: 1447
- 16 Liu J, Li Y.-Q, Zheng W.-J. Monatsh. Chem. 2009; 140: 1425
- 17 Hemantha HP, Sureshbabu VV. Org. Biomol. Chem. 2011; 9: 2597
- 18a Littke AF, Dai CY, Fu GC. J. Am. Chem. Soc. 2000; 122: 4020
- 18b Old DW, Wolfe JP, Buchwald SL. J. Am. Chem. Soc. 1998; 120: 9722
- 19a Han W, Liu C, Jin Z. Adv. Synth. Catal. 2008; 350: 501
- 19b LeBlond CR, Andrews AT, Sun YK, Sowa Jr JR. Org. Lett. 2001; 3: 1555
- 19c Yin L, Zhang Z.-h, Wang Y.-m. Tetrahedron 2006; 62: 9359
- 19d Gallon BJ, Kojima RW, Kaner RB, Diaconescu PL. Angew. Chem. Int. Ed. 2007; 46: 7251; Angew. Chem. 2007, 119, 7389
- 20 Du Q, Zhang W, Ma H, Zheng J, Zhou B, Li Y. Tetrahedron 2012; 68: 3577
- 21 Choudary BM, Madhi S, Chowdari NS, Kantam ML, Sreedhar B. J. Am. Chem. Soc. 2002; 124: 14127