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Synthesis 2019; 51(08): 1803-1808
DOI: 10.1055/s-0037-1611946
DOI: 10.1055/s-0037-1611946
paper
Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-carboxylic Acids
Authors
We are grateful to the National Natural Science Foundation of China (Grant No. 21172142).
Further Information
Publication History
Received: 05 September 2018
Accepted after revision: 17 November 2018
Publication Date:
10 January 2019 (online)
Abstract
A novel decarboxylative N-arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu2O as the catalyst to give the corresponding N-aryl indoles in high yields. This synthetic method shows good functional group tolerance and offers an alternative route to construct N-aryl indoles.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611946.
- Supporting Information (PDF)
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References
- 1 Quirit JG, Lavrenov SN, Poindexter K, Xu J, Kyauk C, Durkin KA, Aronchik I, Tomasiak T, Solomatin YA, Preobrazhenskaya MN, Firestone GL. Biochem. Pharmacol. 2017; 127: 13
- 2 Gueremy C, Audiau F, Champseix A, Uzan A, Le Fur G, Rataud J. J. Med. Chem. 1980; 23: 1306
- 3 Palmer BD, Smaill JB, Boyd M, Boschelli DH, Doherty AM, Hamby JM, Khatana SS, Kramer JB, Kraker AJ, Panek RL, Lu GH, Dahring TK, Winters RT, Showalter HD. H, Denny WA. J. Med. Chem. 1998; 41: 5457
- 4 Zhang H.-C, Derian CK, McComsey DF, White KB, Ye H, Hecker LR, Li J, Addo MF, Croll D, Eckardt AJ, Smith CE, Li Q, Cheung W.-M, Conway BR, Emanuel S, Demarest KT, Andrade-Gordon P, Damiano BP, Maryanoff BE. J. Med. Chem. 2005; 48: 1725
- 5a Ma D, Cai Q. Acc. Chem. Res. 2008; 41: 1450
- 5b Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12564
- 6 Mann G, Hartwig JF, Driver MS, Fernández-Rivas C. J. Am. Chem. Soc. 1998; 120: 827
- 7a Antilla JC, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 11684
- 7b Ziegler DT, Choi J, Muñoz-Molina J, Bissember AC, Peters JC, Fu GC. J. Am. Chem. Soc. 2013; 135: 13107
- 8a Correa A, Bolm C. Angew. Chem. Int. Ed. 2007; 46: 8862
- 8b Guo D, Huang H, Xu J, Jiang H, Liu H. Org. Lett. 2008; 10: 4513
- 8c Alakonda L, Periasamy M. Synthesis 2012; 44: 1063
- 9 Taillefer M, Xia N, Ouali A. Angew. Chem. Int. Ed. 2007; 46: 934
- 10a Teo Y.-C, Yong F.-F, Poh C.-Y, Yan Y.-K, Chua G.-L. Chem. Commun. 2009; 6258
- 10b Yeo Y.-C, Chua G.-L. Chem. Eur. J. 2009; 15: 3072
- 10c Murthy SN, Madhav B, Reddy VP, Nageswar YV. D. Adv. Synth. Catal. 2010; 352: 3241
- 11a Yuan Y, Thomé I, Kim SH, Chen D, Beyer A, Bonnamour J, Zuidema E, Chang S, Bolm C. Adv. Synth. Catal. 2010; 352: 2892
- 11b Cano R, Ramón DJ, Yus M. J. Org. Chem. 2011; 76: 654
- 11c Chen J, Wu J. Angew. Chem. Int. Ed. 2017; 56: 3951
- 12a Guo X.-X. J. Org. Chem. 2013; 78: 1660
- 12b Gu D.-W, Guo X.-X. Org. Biomol. Chem. 2014; 12: 6114
- 12c Guo X.-X, Gu D.-W, Wu Z, Zhang W. Chem. Rev. 2015; 115: 1622
- 12d Xu N, Gu D.-W, Zi J, Wu X.-Y, Guo X.-X. Org. Lett. 2016; 18: 2439
- 13a Melikhova EY, Pullin RD. C, Winter C, Donohoe TJ. Angew. Chem. Int. Ed. 2016; 55: 9753
- 13b Yuan X, Yao J.-F, Tang Z.-Y. Org. Lett. 2017; 19: 1410
- 13c Noda H, Furutachi M, Asada Y, Shibasaki M, Kumagai N. Nat. Chem. 2017; 9: 571
- 13d Cruciani G, Milani N, Benedetti P, Lepri S, Cesarini L, Baroni M, Spyrakis F, Tortorella S, Mosconi E, Goracci L. J. Med. Chem. 2018; 61: 360
- 13e Zhang T.-Y, Liu C, Chen C, Liu J.-X, Xiang H.-Y, Jiang W, Ding T.-M, Zhang S.-Y. Org. Lett. 2018; 20: 220
- 14a Olgen S, Akaho E, Nebioglu D. Eur. J. Med. Chem. 2001; 36: 747
- 14b Bennasar M.-L, Roca T, Ferrando F. Tetrahedron Lett. 2004; 45: 5605
- 15a Goossen LJ, Rodríguez N, Melzer B, Linder C, Deng G, Levy LM. J. Am. Chem. Soc. 2007; 129: 4824
- 15b Fromm A, van Wüllen C, Hackenberger D, Gooßen LJ. J. Am. Chem. Soc. 2014; 136: 10007
- 16a Cristau H.-J, Cellier PP, Spindler J.-F, Taillefer M. Chem. Eur. J. 2004; 10: 5607
- 16b Zhang H, Cai Q, Ma D. J. Org. Chem. 2005; 70: 5164
- 17 Chen H, Lei M, Hu L. Tetrahedron 2014; 70: 5626
- 18 Elliott E.-C, Bowkett ER, Maggs JL, Bacsa J, Park BK, Regan SL, O’Neill PM, Stachulski AV. Org. Lett. 2011; 13: 5592
- 19 Hong X, Tan Q, Liu B, Xu B. Angew. Chem. Int. Ed. 2017; 56: 3961
- 20 Willis MC, Brace GN, Findlay TJ. K, Holmes IP. Adv. Synth. Catal. 2006; 348: 851
- 21 Yong F.-F, Teo Y.-C, Tay S.-H, Tan BY.-H, Lim K.-H. Tetrahedron Lett. 2011; 52: 1161
- 22 Old DW, Harris MC, Buchwald SL. Org. Lett. 2000; 2: 1403
- 23 Xiao R, Zhao H, Cai M. Tetrahedron 2013; 69: 5444
For reviews, see:
For selected examples, see:
An example of copper(II)-catalyzed coupling of indole-2-carboxylic acid with bromobenzene giving 1-phenyl-indole-2-carboxylic acid has been reported, see: