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Synthesis 2013; 45(10): 1373-1379
DOI: 10.1055/s-0032-1316872
DOI: 10.1055/s-0032-1316872
paper
Copper-Impregnated Magnetite as a Heterogeneous Catalyst for the Homocoupling of Terminal Alkynes
Further Information
Publication History
Received: 29 January 2013
Accepted after revision: 03 March 2013
Publication Date:
14 March 2013 (online)
Abstract
Copper-impregnated magnetite is a versatile heterogeneous catalytic system for the synthesis of 1,3-diynes by the homocoupling of terminal alkynes. This catalyst does not require the use of pressurized oxygen as the oxidant and it does not need a solvent or harsh conditions to give the expected products. Moreover, the catalyst can be removed from the reaction medium simply by using a magnet. The reaction occurs at the lowest copper loading reported for any heterogeneous catalyst.
Key words
alkynes - copper - heterogeneous catalysis - iron - supported catalysis - coupling - furansSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Modern Acetylene Chemistry . Stang PJ, Diederich F. VCH; Weinheim: 1995
- 1b Brandsma L. Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques. Elsevier; Oxford: 2004
- 1c Acetylene Chemistry . Diederich F, Stang PJ, Tykwinski RR. Wiley-VCH; Weinheim: 2005
- 2 Shi Shun AL. K, Tykwinski RR. Angew. Chem. Int. Ed. 2006; 45: 1034
- 3a Neenan TX, Whitesides GM. J. Org. Chem. 1988; 53: 2489
- 3b Tour JM. Chem. Rev. 1996; 96: 537
- 3c Bunz UH. F, Rubin Y, Tobe Y. Chem. Soc. Rev. 1999; 28: 107
- 4a Ladika M, Fisk TE, Wu WW, Jons SD. J. Am. Chem. Soc. 1994; 116: 12093
- 4b Ohkita M, Ando K, Suzuki T, Tsuji T. J. Org. Chem. 2000; 65: 4385
- 4c Marsden JA, Haley MM. J. Org. Chem. 2005; 70: 10213
- 5 Crowley JD, Goldup SM, Lee A.-L, Leigh DA, McBurney RT. Chem. Soc. Rev. 2009; 38: 1530
-
6a Siemsen P, Livingston C, Diederich F. Angew. Chem. Int. Ed. 2000; 39: 2632
- 6b Stefani HA, Guarezemini AS, Cella R. Tetrahedron 2010; 66: 7871
- 6c Alonso F, Yus M. ACS Catal. 2012; 2: 1441
- 8a Yadav JS, Reddy BV. S, Reddy KB, Gayathri KU, Prasad AR. Tetrahedron Lett. 2003; 44: 6493
- 8b Lu X, Zhang Y, Luo C, Wang Y. Synth. Commun. 2006; 36: 2503
- 8c Jiang H.-F, Tang J.-Y, Wang A.-Z, Deng G.-H, Yang S.-R. Synthesis 2006; 1155
- 8d Kumar V, Chipeleme A, Chibale K. Eur. J. Org. Chem. 2008; 43
- 8e Yin K, Li C, Li J, Jia X. Green Chem. 2011; 13: 591
- 8f Zhang S, Liu X, Wang T. Adv. Synth. Catal. 2011; 353: 1463
- 8g Schmidt R, Thorwirth R, Szuppa T, Stolle A, Ondruschka B, Hopf H. Chem. Eur. J. 2011; 17: 8129
- 9a Toda F, Tokumaru Y. Chem. Lett. 1990; 987
- 9b Nador F, Fortunato L, Moglie Y, Vitale C, Radivoy G. Synthesis 2009; 4027
- 9c Wang D, Li J, Li N, Gao T, Hou S, Chen B. Green Chem. 2010; 12: 45
- 10a Auer SM, Schneider M, Baiker A. J. Chem. Soc., Chem. Commun. 1995; 2057
- 10b Auer SM, Wandeler R, Göbel U, Baiker A. J. Catal. 1997; 169: 1
- 10c Zhu BC, Jiang XZ. Appl. Organomet. Chem. 2007; 21: 345
- 11 Sharifi A, Mirzaei M, Naimi-Jamal MR. Monatsh. Chem. 2006; 137: 213
- 12 Kuhn P, Alix A, Kumarraja M, Louis B, Pale P, Sommer J. Eur. J. Org. Chem. 2009; 423
- 13a Oishi T, Katayama T, Yamaguchi K, Mizuno N. Chem. Eur. J. 2009; 15: 7539
- 13b Alonso F, Melkonian T, Moglie Y, Yus M. Eur. J. Org. Chem. 2011; 2524
- 14 Kamata K, Yamaguchi S, Kotani M, Yamaguchi K, Mizuni N. Angew. Chem. Int. Ed. 2008; 47: 2407
- 15 Oishi T, Yamaguchi K, Mizuno N. ACS Catal. 2011; 1: 1351
- 16 Xiao R, Yao R, Cai M. Eur. J. Org. Chem. 2012; 4178
- 17 Meng X, Li C, Han B, Wang T, Chen B. Tetrahedron 2010; 66: 4029
- 18a Cano R, Ramón DJ, Yus M. Tetrahedron 2011; 67: 5432
- 18b Cano R, Ramón DJ, Yus M. J. Org. Chem. 2011; 76: 5547
- 18c Cano R, Yus M, Ramón DJ. Tetrahedron 2011; 67: 8079
- 18d Cano R, Yus M, Ramón DJ. ACS Catal. 2012; 2: 1070
- 18e Cano R, Yus M, Ramón DJ. Chem. Commun. (Cambridge) 2012; 48: 7628
- 19a Martínez R, Ramón DJ, Yus M. Adv. Synth. Catal. 2008; 350: 1235
- 19b Martínez R, Ramón DJ, Yus M. Org. Biomol. Chem. 2009; 7: 2176
- 19c Cano R, Yus M, Ramón DJ. Synlett 2011; 2017
- 20a Aliaga MJ, Ramón DJ, Yus M. Org. Biomol. Chem. 2010; 8: 43
- 20b Cano R, Ramón DJ, Yus M. J. Org. Chem. 2010; 75: 3458
- 20c Cano R, Yus M, Ramón DJ. Tetrahedron 2012; 68: 1393
- 20d Pérez JM, Cano R, Yus M, Ramón DJ. Eur. J. Org. Chem. 2012; 4548
- 21 Jiang H, Zeng W, Li Y, Wu W, Huang L, Fu W. J. Org. Chem. 2012; 77: 5179
- 22 Yu M, Pan D, Jia W, Chen W, Jiao N. Tetrahedron Lett. 2010; 51: 1287
- 23 Feng X, Zhao Z, Yang F, Jin T, Ma Y, Bao M. J. Org. Chem. 2011; 696: 1479
- 24 Kude K, Hayase S, Kawatsura M, Itoh T. Heteroat. Chem. 2011; 22: 397
- 25 Mizuno N, Kamata K, Nagakawa Y, Oishi T, Yamaguchi K. Catal. Today 2010; 157: 359
- 26 Cheng T.-P, Liao B.-S, Liu Y.-H, Peng S.-M, Liu S.-T. Dalton Trans. 2012; 41: 3468
-
27 Nun P, Dupuy S, Gaillard S, Poater A, Cavallo L, Nolan SP. Catal. Sci. Technol. 2011; 1: 58
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