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Synthesis 2014; 46(21): 2951-2956
DOI: 10.1055/s-0034-1378556
DOI: 10.1055/s-0034-1378556
paper
A Novel Approach for the Synthesis of Biologically Important N-Aryl Amides with Arenediazonium Salts
Further Information
Publication History
Received: 10 May 2014
Accepted after revision: 10 July 2014
Publication Date:
13 August 2014 (online)
Abstract
A novel protocol has been developed for the synthesis of N-aryl amides from arenediazonium salts and primary amides. Tetrabutylammonium iodide was used as an iodide source for in situ formation of iodobenzene. The reaction was catalyzed by using inexpensive copper(I) iodide. The protocol is widely applicable to a variety of substituted amides and diazonium salts, giving good to excellent yields of the desired products.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References and Notes
- 1a Beletskaya IP, Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337
-
1b Beccalli EM, Broggini G, Martinelli M, Sottocornola S. Chem. Rev. 2007; 107: 5318
- 1c Negwer M. Organic-Chemical Drugs and their Synonyms: An International Survey. Akademie-Verlag; Berlin: 1994. 7th ed.
- 1d Montgomery JH. Agrochemicals Desk Reference: Environmental Data . Lewis Publishers; Chelsea: 1993
- 1e Corbert JP, Mignani G. Chem. Rev. 2006; 106: 2651
-
1f Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
- 1g Craig PN In Comprehensive Medicinal Chemistry: The Rational Design, Mechanistic Study and Therapeutic Application of Chemical Compounds. Vol. 8. Drayton CJ. Pergamon; Oxford: 1991: 730
- 1h Dictionary of Natural Products . Vol. 1. Buckingham JB. Chapman and Hall; London: 1994
- 2a Malawska B. Curr. Top. Med. Chem. 2005; 5: 69
- 2b Luszczki JJ, Swiader MJ, Swiader K, Paruszewski R, Turski WA, Czuczwar SJ. Fundam. Clin. Pharmacol. 2008; 22: 69
- 3a Sawant P, Maier ME. Eur. J. Org. Chem. 2012; 6576
- 3b Kawato Y, Chaudhary S, Kumagai N, Shibasaki M. Chem. Eur. J. 2013; 19: 3802
- 4a Tran AT, Nicholas DW, West P, Baker EN, Britton WJ, Payne RJ. Org. Biomol. Chem. 2013; 11: 8113
- 4b Zitko J, Servusová B, Paterová P, Mandiková J, Kubíček V, Kučera R, Hrabcová V, Kuneš J, Soukup O, Doležal M. Molecules 2013; 18: 14807
- 5a Wamser CC, Yates JA. J. Org. Chem. 1989; 54: 150
- 5b Ueda S, Nagasawa H. J. Org. Chem. 2009; 74: 4272
- 5c Dumbre DK, Choudhary VR. Catal. Commun. 2011; 12: 1351
- 5d Ganai S, Majumdar KC. Synthesis 2013; 45: 2619
- 5e Paul S, Nanda P, Gupta R. Molecules 2003; 8: 374
- 5f Shi F, Li J, Li C, Jia X. Tetrahedron Lett. 2010; 51: 6049
- 5g Li Y, Li Z, Xiong T, Zhang Q, Zhang X. Org. Lett. 2012; 14: 3522
- 6a Zheng Z.-J, Ye F, Zheng L.-S, Yang K.-F, Lai G.-Q, Xu L.-W. Chem. Eur. J. 2012; 18: 14094
- 6b Hosseinzadeh R, Tajbakhsh M, Mohadjerani M, Mehdinejad H. Synlett 2004; 1517
- 6c Chandrasekhar S, Sultana SS, Yaragorla SR, Reddy NR. Synthesis 2006; 839
- 6d Jammi S, Sekarpandi S, Rout L, Mukherjee T, Mandal S, Mitra R, Saha P, Punniyamurthy T. J. Org. Chem. 2009; 74: 1971
- 6e Teo Y.-C. Adv. Synth. Catal. 2009; 351: 720
- 6f Yao Z, Wei X. Chin. J. Chem. 2010; 28: 2260
- 7 Islam SM, Mondal S, Mondal P, Roy AS, Tuhina K, Salam N, Mobarak M. J. Organomet. Chem. 2012; 696: 4264
- 8 Fedorov AY, Finet J.-P. Tetrahedron Lett. 1999; 40: 2747
- 9 Lam PY. S, Vincent G, Bonne D, Clark CG. Tetrahedron Lett. 2002; 43: 3091
- 10 Lopez-Alvarado P, Avendano C, Menendez JC. J. Org. Chem. 1995; 60: 5678
- 11 Kang S.-K, Lee S.-H, Lee D. Synlett 2000; 1022
- 12a Lam PY. S, Deudon S, Hauptman E, Clark CG. Tetrahedron Lett. 2001; 42: 2427
- 12b Lin B, Liu M, Ye Z, Ding J, Wu H, Cheng J. Org. Biomol. Chem. 2009; 7: 869
- 13a Anctill EJ. G, Snieckus V In Metal-Catalyzed Cross-Coupling Reactions . Vol. 2. De Mejijere A, Diederich F. Wiley-VCH; Weinheim: 2004: 761
- 13b Mitchell TN In Metal-Catalyzed Cross-Coupling Reactions . Vol. 1. De Mejijere A, Diederich F. Wiley-VCH; Weinheim: 2004: 125
- 14a Ikawa T, Barder TE, Biscoe MR, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 13001
- 14b Yin J, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 6043
- 14c Dooleweerdt K, Fors BP, Buchwald SL. Org. Lett. 2010; 12: 2350
- 15 Teo Y.-C, Chua G.-L. Chem. Eur. J. 2009; 15: 3072
- 16a Correa A, Elmore S, Bolm C. Chem. Eur. J. 2008; 14: 3527
- 16b Bolm C, Correa A. Angew. Chem. Int. Ed. 2007; 46: 8862
- 17 Raghuvanshi DS, Gupta AK, Singh KN. Org. Lett. 2012; 14: 4326
- 18 Das R, Mandal M, Chakraborty D. Asian J. Org. Chem. 2013; 2: 579
- 19 Gooßen LJ, Blanchot M, Salih FS. M, Gooßen K. Synthesis 2009; 2283
- 20a Wolf C, Xu H. Chem. Commun. 2009; 1715
- 20b Swapna K, Murthy SN, Nageswar YV. D. Eur. J. Org. Chem. 2010; 6678
- 20c Teo Y.-C, Yong F.-F, Ithnin IK, Yio TS.-H, Lin Z. Eur. J. Org. Chem. 2013; 515
- 20d Jammi S, Krishnamoorthy S, Saha P, Kundu DS, Sakthivel S, Ali MA, Paul R, Punniyamurthy T. Synlett 2009; 3323
- 20e Moriwaki K, Satoh K, Takada M, Ishino Y, Ohno T. Tetrahedron Lett. 2005; 46: 7559
- 20f Ali MA, Shaha P, Punniyamurthy T. Synthesis 2010; 908
- 21a Kuethe JT, Childers KG. Adv. Synth. Catal. 2008; 350: 1577
- 21b Felpin F.-X, Fouquet E, Zakri C. Adv. Synth. Catal. 2009; 351: 649
- 21c Li X, Yan X.-Y, Chang H.-H, Wang L.-C, Zhang Y, Chen W.-W, Li Y.-W, Wei W.-L. Org. Biomol. Chem. 2012; 10: 495
- 21d Andrus MB, Song C. Org. Lett. 2001; 3: 3761
- 21e Masllorens J, González I, Roglans A. Eur. J. Org. Chem. 2007; 158
- 22 Kikukawa K, Kono K, Wada F, Matsuda T. J. Org. Chem. 1983; 48: 1333
-
23a Panda B, Sarkar TK. Chem. Commun. 2010; 46: 3131
-
23b Fabrizi G, Goggiamani A, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed. 2010; 49: 4067
- 24a Felpin F.-X, Fouquet E, Zakri C. Adv. Synth. Catal. 2008; 350: 2559
- 24b Felpin F.-X, Ibarguren O, Hardy LN, Fouquet E. J. Org. Chem. 2009; 74: 1349
- 24c Machado AH. L, de Sousa MA, Patto DC. S, Azevedo LF. S, Bombonato FI, Correia CR. D. Tetrahedron Lett. 2009; 50: 1222
- 24d Schmidt B, Hölter F. Chem. Eur. J. 2009; 15: 11948
- 24e Cacchi S, Fabrizi G, Goggiamani A, Sferrazza A. Synlett 2009; 973
- 24f Pastre JC, Correia CR. D. Adv. Synth. Catal. 2009; 351: 1217
For selected reference on copper-catalyzed reactions, see: