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Synthesis 2013; 45(22): 3151-3156
DOI: 10.1055/s-0033-1339659
DOI: 10.1055/s-0033-1339659
paper
Solvent- and Ligand-Free Palladium-Catalyzed Amination of Aryl Halides
Further Information
Publication History
Received: 03 June 2013
Accepted after revision: 01 August 2013
Publication Date:
06 September 2013 (online)
Abstract
An environmentally friendly and economically favorable approach to the formation of C–N bonds is presented. The methodology is particularly interesting in that the reaction is realized under both solvent- and ligand-free conditions and involves the use of a low loading of a palladium catalyst dispersed with the reactants on a suitable solid support. The reaction proceeds rapidly under microwave irradiation.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Müller TE, Beller M. Chem. Rev. 1998; 98: 675
- 1b Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M. Chem. Rev. 2008; 108: 3795
- 1c Kienle M, Dubbaka SR, Brade K, Knochel P. Eur. J. Org. Chem. 2007; 4166
- 1d Kotov V, Scarborough CC, Stahl SS. Inorg. Chem. 2007; 46: 1910
- 1e Wolfe JP. Eur. J. Org. Chem. 2007; 571
- 1f Minatti A, Muniz K. Chem. Soc. Rev. 2007; 36: 1142
- 1g Hesp KD, Stradiotto M. ChemCatChem 2011; 2: 1346
- 2a The Chemistry and Application of Dyes . Waring DR, Hallas G. Plenum; New York: 1990
- 2b Hili R, Yudin AK. Nat. Chem. Biol. 2006; 2: 284
- 2c D’Aprano G, Leclerc M, Zott G, Schiavon G. Chem. Mater. 1995; 7: 33
- 2d He F, Foxman BM, Snider BB. J. Am. Chem. Soc. 1998; 120: 6417
- 3a Buchwald SL, Mauger C, Mignani G, Scholz U. Adv. Synth. Catal. 2006; 348: 23
- 3b Corbet JP, Mignani G. Chem. Rev. 2006; 106: 2651
- 3c Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338 ; Angew. Chem. 2008, 120, 6438
- 3d Busacca CA, Fandrick DR, Song JJ, Senanayake CH. Adv. Synth. Catal. 2011; 353: 1825
- 3e Martin R, Buchwald SL. Acc. Chem. Res. 2008; 41: 1461
- 3f Hartwig JF. Angew. Chem. Int. Ed. 1998; 37: 2046 ; Angew. Chem. 1998, 110, 2154
- 4a Guram AS, Rennels RA, Buchwald SL. Angew. Chem. Int. Ed. 1995; 34: 1348 ; Angew. Chem. 1995, 107, 1456
- 4b Louie J, Hartwig JF. Tetrahedron Lett. 1995; 36: 3609
- 5 Hartwig JF. Organotransition Metal Chemistry: From Bonding to Catalysis . University Science Books; Sausalito: 2010
- 6a Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
- 6b Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
- 6c Hartwig JF, Kawatsura M, Hauck SI, Shaughnessy KH, Alcazar-Roman LM. J. Org. Chem. 1999; 64: 5575
- 6d Watanabe M, Nishiyama M, Yamamoto T, Koie Y. Tetrahedron Lett. 2000; 41: 481
- 6e Old DW, Harris MC, Buchwald SL. Org. Lett. 2000; 2: 1403
- 6f Tardiff BJ, McDonald R, Ferguson MJ, Stradiotto M. J. Org. Chem. 2012; 77: 1056
- 6g Tardiff BJ, Stradiotto M. Eur. J. Org. Chem. 2012; 3972
- 6h Chen L, Yu G.-A, Li F, Zhu X, Zhang B, Guo R, Li X, Yang Q, Jin S, Liu C, Liu S.-H. J. Organomet. Chem. 2010; 695: 1768
- 7a Dong JJ, Roger J, Pozgan F, Doucet H. Green Chem. 2009; 11: 1832
- 7b de Vries AH. M, Parlevliet FJ, Schmieder-van de Vondervoort L, Mommers JH. M, Henderickx HJ. W, Walet MA. M, de Vries JG. Adv. Synth. Catal. 2002; 344: 996
- 7c Beletskaya IP, Kashin AN, Karlstedt NB, Mitin AV, Cheprakov AV, Kazankov GM. J. Organomet. Chem. 2001; 622: 89
- 7d de Vries AH. M, Mulders JM. C. A, Mommers JH. M, Henderickx HJ. W, de Vries JG. Org. Lett. 2003; 5: 3285
- 7e Gruber AS, Zim D, Ebeling G, Monteiro AL, Dupont J. Org. Lett. 2000; 2: 1287
- 7f Alonso DA, Najera C, Pacheco MC. Org. Lett. 2000; 2: 1823
- 7g Beccalli EM, Borsini E, Brenna S, Galli S, Rigamonti M, Broggini G. Chem. Eur. J. 2010; 16: 1670
- 7h Sun P, Qu X, Li T, Zhu Y, Yang HL, Xing ZY, Mao JC. Synlett 2012; 23: 150
- 8a Basolo L, Beccalli EM, Borsini E, Broggini G. Tetrahedron 2009; 65: 3486
- 8b Bellina F, Benelli F, Rossi R. J. Org. Chem. 2008; 73: 5529
- 8c Wang X, Gribkov DV, Sames DJ. J. Org. Chem. 2007; 72: 1476
- 8d Roger J, Doucet H. Adv. Synth. Catal. 2009; 351: 1977
- 8e Fu H, Chen L, Doucet H. J. Org. Chem. 2012; 77: 4473
- 8f Wenig F, Wang C, Xu B. Tetrahedron Lett. 2010; 51: 2593
- 8g Bheeter CB, Bera JK, Doucet H. Adv. Synth. Catal. 2012; 354: 3533
- 9a Orito K, Horibata A, Nakamura T, Ushito H, Nagasaki H, Yuguchi M, Yamashita S, Tokuda M. J. Am. Chem. Soc. 2004; 126: 14342
- 9b Orito K, Miyazawa M, Nakamura T, Horibata A, Ushito H, Nagasaki H, Yuguchi M, Yamashita S, Yamazaki T, Tokuda M. J. Org. Chem. 2006; 71: 5951
- 9c Wada Y, Nagasaki H, Tokuda M, Orito K. J. Org. Chem. 2007; 72: 2008
- 9d Yamashita S, Kurono N, Senboku H, Tokuda M, Orito K. Eur. J. Org. Chem. 2009; 1173
- 10a Velmathi S, Vijayaraghavan R, Amarendar C, Pal RP, Vinu A. Synlett 2010; 2733
- 10b Jiang Z, She J, Lin X. Adv. Synth. Catal. 2009; 351: 2558
- 11a Al-Amin M, Honma T, Hoshiya N, Shuto S, Arisawa M. Adv. Synth. Catal. 2012; 354: 1061
- 11b Guha BN. R, Shil AK, Sharma D, Das P. Tetrahedron Lett. 2012; 53: 5318
- 12a Correa A, Bolm C. Adv. Synth. Catal. 2007; 349: 2673
- 12b Zhu R, Xing L, Wang X, Cheng C, Su D, Hu Y. Adv. Synth. Catal. 2008; 350: 1253
- 12c Bellina F, Calandri C, Cauteruccio S, Rossi R. Eur. J. Org. Chem. 2007; 2147
- 12d Chang JW. W, Xu X, Chan PW. H. Tetrahedron Lett. 2007; 48: 245
- 12e Sperotto E, de Vries JG, van Klink GP. M, van Koten G. Tetrahedron Lett. 2007; 48: 7366
- 12f Yong FF, Teo YC. Synlett 2010; 3068
- 12g Teo YC, Yong FF. Synlett 2011; 837
- 12h Azzaro S, Desage-El Murr M, Fensterbank L, Lacôte E, Malacria M. Synlett 2011; 849
- 12i He H, Wu YJ. Tetrahedron Lett. 2003; 44: 3385
- 12j Gavade S, Shingare M, Mane D. Bull. Korean Chem. Soc. 2011; 32: 4167
- 13a Abbiati G, Beccalli EM, Broggini G, Martinelli M, Paladino G. Synlett 2006; 73
- 13b Basolo L, Beccalli EM, Borsini E, Broggini G, Khansaa M, Rigamonti M. Eur. J. Org. Chem. 2010; 9: 1694
- 13c Beccalli EM, Bernasconi A, Borsini E, Broggini G, Rigamonti M, Zecchi G. J. Org. Chem. 2010; 75: 6923
- 13d Borsini E, Broggini G, Fasana A, Galli S, Khansaa M, Piarulli U, Rigamonti M. Adv. Synth. Catal. 2011; 353: 985
- 13e Broggini G, Barbera V, Beccalli EM, Borsini E, Galli S, Lanza G, Zecchi G. Adv. Synth. Catal. 2012; 354: 159
- 13f Broggini G, Borsini E, Fasana A, Poli G, Liron F. Eur. J. Org. Chem. 2012; 3617
- 13g Broggini G, Barbera V, Beccalli EM, Cacchio U, Fasana A, Galli S, Gazzola S. Adv. Synth. Catal. 2013; 355: 1640
- 14 Basolo L, Bernasconi A, Borsini E, Broggini G, Beccalli EM. ChemSusChem 2011; 4: 1637
- 15 Chatani N, Asaumi T, Yorimitsu S, Ikeda T, Kakiuchi F, Murai S. J. Am. Chem. Soc. 2001; 123: 10935
- 16 Chatani N, Yorimitsu S, Asaumi T, Kakiuchi F, Murai S. J. Org. Chem. 2002; 67: 7557
- 17 Beller M, Breindl C, Riermeier TH, Eichberger M, Trauthwein H. Angew. Chem. Int. Ed. 1998; 37: 3389
- 18 Omar-Amrani R, Schneider R, Fort Y. Synthesis 2004; 2527
- 19a Urgaonkar S, Xu JH, Verkade JG. J. Org. Chem. 2003; 68: 8416
- 19b Urgaonka S, Verkade JG. J. Org. Chem. 2004; 69: 9135
- 20 Shiraishi M, Kitayoshi T, Aramaki Y, Honda S, Oda T. WO 9932468, 1999
- 21 During the reaction of ethyl pyridin-2-ylcarbamate, hydrolysis of the ester group occurred and compound 12 was isolated; see: Fang Y, Larock RC. Tetrahedron 2012; 68: 2819
- 22 Xu ZL, Li HX, Ren ZG, Du WY, Xu WC, Lang JP. Tetrahedron 2011; 67: 5282
- 23 Meneyrol J, Helissey P, Tratrat C, Giorgi-Renault S, Husson H.-P. Synth. Commun. 2001; 31: 987
- 24 Yang K, Qiu Y, Jiang S, Wang Z, Li Z. J. Org. Chem. 2011; 76: 3151
- 25 Shan Y, Wang Y, Jia X, Cai W, Xiang J. Synth. Commun. 2012; 42: 1192
- 26 Fairlamb IJ. S, Kapdi AR, Lee AF, McGlacken GP, Weissburger F, de Vries AH. M, Schmieder-van de Vondervoort L. Chem. Eur. J. 2006; 12: 8750
For ligand-free Heck reactions, see:
For ligand-free arylation reactions, see:
For ligand-free carbonylation reactions, see:
For ligand-free copper-catalyzed amination reactions, see: