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Synthesis 2017; 49(08): 1834-1838
DOI: 10.1055/s-0036-1588373
DOI: 10.1055/s-0036-1588373
paper
Synthesis of N-Aryl Amides by Ligand-Free Copper-Catalyzed ipso-Amidation of Arylboronic Acids with Nitriles
Further Information
Publication History
Received: 13 September 2016
Accepted after revision: 21 November 2016
Publication Date:
16 December 2016 (online)
Abstract
A facile copper-catalyzed ipso-amidation of arylboronic acids with nitriles has been developed. The method provides a highly efficient and economical synthesis of N-aryl amides with a broad substrate scope.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588373.
- Supporting Information
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References
- 1a The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science. Greenberg A, Breneman CM, Liebman JF. Wiley; New York: 2002
- 1b Sewald N, Jakubke HD. Peptides: Chemistry and Biology . 2nd ed. Wiley-VCH; Weinheim: 2009
- 1c Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
- 1d Allen CL, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
- 1e El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
- 1f Zhang D.-W, Zhao X, Hou J.-L, Li Z.-T. Chem. Rev. 2012; 112: 5271
- 1g García-Álvarez R, Crochet P, Cadierno V. Green Chem. 2013; 15: 46
- 2a Ishida J, Yamamoto H, Kido Y, Kamijo K, Murano K, Miyake H, Ohkubo M, Kinoshita T, Warizaya M, Iwashita A, Mihara K, Matsuokac N, Hattori K. Bioorg. Med. Chem. 2006; 14: 1378
- 2b Lehtiö L, Jemth AS, Collins R, Loseva O, Johansson A, Markova N, Hammarström M, Flores A, Holmberg-Schiavone L, Weigelt J, Helleday T, Schüler H, Karlberg T. J. Med. Chem. 2009; 52: 3108
- 2c Gracia SR, Gaus K, Sewald N. Future Med. Chem. 2009; 1: 1289
- 3 Zhou X, Wang L, Li Z. Adv. Synth. Catal. 2012; 354: 584
- 4a Klapars A, Antilla JC, Huang X, Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
- 4b Huang X, Anderson KW, Zim D, Jiang L, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 6653
- 4c Xu H, Wolf C. Chem. Commun. 2009; 1715
- 4d Cheng C, Sun G, Wan J, Sun C. Synlett 2009; 2663
- 4e Ali MA, Saha P, Punniyamurthy T. Synthesis 2010; 908
- 4f Kumar A, Bishnoi AK. RSC Adv. 2014; 4: 41631
- 5 Wang J, Yin X, Wu J, Wu D, Pan J. Tetrahedron 2013; 69: 10463
- 6a Zhang D.-X, Xiang S.-K, Hu H, Tan W, Feng C, Wang B.-Q. Tetrahedron 2013; 69: 10022
- 6b Xiang S.-K, Zhang D.-X, Hu H, Shi J.-L, Liao L.-G, Feng C, Wang B.-Q, Zhao K.-Q, Hu P, Yang H, Yu W.-H. Adv. Synth. Catal. 2013; 355: 1495
- 7a Hsieh J.-C, Cheng A.-Y, Fua J.-H, Kanga T.-W. Org. Biomol. Chem. 2012; 10: 6404
- 7b Chen Y.-F, Wu Y.-S, Jhan Y.-H, Hsieh J.-C. Org. Chem. Front. 2014; 1: 253
- 8 McPherson CG, Livingstone K, Jamieson C, Simpson I. Synlett 2016; 27: 88
- 9a Chan DM. T, Kevin LM, Wang R.-P, Michael PW. Tetrahedron Lett. 1998; 39: 2933
- 9b Evans DA, Katz JL, West TR. Tetrahedron Lett. 1998; 39: 2937
- 9c Lam PY. S, Charles CG, Saubern S, Adams J, Winters MP. W, Chan DM. T, Combs A. Tetrahedron Lett. 1998; 39: 2941
- 10 Prakash GK. S, Moran MD, Mathew T, Olah GA. J. Fluorine Chem. 2009; 130: 806
- 11 Huang H, Jiang Z.-T, Wu Y, Gan C.-Y, Li J.-M, Xiang S.-K, Feng C, Wang B.-Q, Tang W.-T. Synlett 2016; 27: 951
- 12 Midya GC, Kapat A, Maiti S, Dash J. J. Org. Chem. 2015; 80: 4148
- 13 Zhang L, Su S, Wu H, Wang S. Tetrahedron 2009; 65: 10022
- 14 Deshidi R, Rizvi MA, Shah BA. RSC Adv. 2015; 5: 90521
- 15 Liu Z, Zhang X, Li J, Li F, Li F, Jia X, Li J. Org. Lett. 2016; 18: 4052
- 16 Tan BY.-H, Teo Y.-C. Org. Biomol. Chem. 2014; 12: 7478
- 17 Fan W, Yang Y, Lei J, Jiang Q, Zhou W. J. Org. Chem. 2015; 80: 8782
- 18 Hellwinkel D, Lämmerzahl F, Hofmann G. Chem. Ber. 1983; 116: 3375
- 19 Wang Y, Zhu D, Tang L, Wang S, Wang Z. Angew. Chem. Int. Ed. 2011; 50: 8917
- 20 Verma A, Patel S, , Meenakshi Kumar A, Yadav A, Kumar S, Jana S, Sharma S, Prasad CD, Kumar S. Chem. Commun. 2015; 51: 1371
- 21 Zhu W, Haupenthal J, Groh M, Fountain M, Hartmann RW. Antimicrob. Agents Chemother. 2014; 58: 4242
- 22 Jóźwiak A, Brzeziński JZ, Płotka MW, Szcześniak AK, Malinowski Z, Epsztajn J. Eur. J. Org. Chem. 2004; 3254
- 23 Takács A, Jakab B, Petz A, Kollár L. Tetrahedron 2007; 63: 10372
- 24 Nielsen DR, McEwen WE. J. Am. Chem. Soc. 1954; 76: 4042
- 25 Stevens CL, Gasser RJ. J. Am. Chem. Soc. 1957; 79: 6057
- 26 Gowda S, Gowda BK. K, Gowda DC. Synth. Commun. 2003; 33: 281
- 27 Hause CR, Hoffenberg DS. J. Am. Chem. Soc. 1955; 77: 4885
- 28 Fors BP, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 15914
- 29 Suresh Babu VV, Vasanthakumar G.-R, Tantry SJ. Tetrahedron Lett. 2005; 46: 4099
- 30 Gaber AE.-A. M, Muathen HA, Taib LA. J. Anal. Appl. Pyrol. 2011; 91: 119
- 31 Ueda S, Nagasawa H. J. Org. Chem. 2009; 74: 4272
- 32 Racine E, Monnier F, Vors J.-P, Taillefer M. Org. Lett. 2011; 13: 2818
- 33 Weitzberg M, Aizenshtat Z, Blum J. J. Heterocycl. Chem. 1981; 18: 1513
- 34 Al-Masun M, Wai MC, Dunnenberger H. Synth. Commun. 2011; 41: 2888
- 35 Lunn G, Sansone EB. J. Org. Chem. 1986; 51: 513
- 36 Zhu M, Zheng N. Synthesis 2011; 2223
- 37 Mosher WA, Kehr CL. J. Am. Chem. Soc. 1953; 75: 3172