Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(01): 42-48
DOI: 10.1055/s-0034-1379073
DOI: 10.1055/s-0034-1379073
paper
An Iron and Copper System Catalyzed C–H Arylation of Azoles with Arylboronic Acids
Further Information
Publication History
Received: 09 May 2014
Accepted after revision: 11 August 2014
Publication Date:
29 September 2014 (online)
Abstract
An efficient, environmentally friendly, and economical new method for arylation reactions of azoles with arylboronic acids via copper–iron-catalyzed C–H and C–B bond activation has been developed. The protocol tolerates a series of functional groups, such as methoxy, nitro, cyano, chloro, and trifluoromethyl groups.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Tzanopoulou S, Sagnou M, Paravatou-Petsotas M, Gourni E, Loudos G, Xanthopoulos S, Lafkas D, Kiaris H, Varvarigou A, Pirmettis IC, Papadopoulos M, Pelecanou M. J. Med. Chem. 2010; 53: 4633
- 1b Van Zandt MC, Jones ML, Gunn DE, Geraci LS, Jones JH, Sawicki DR, Sredy J, Jacot JL, DiCioccio AT, Petrova T, Mitschler A, Podjarny AD. J. Med. Chem. 2005; 48: 3141
- 1c Katz L. J. Am. Chem. Soc. 1953; 75: 712
- 1d Dalvie DK, Kalgutkar AS, Khojasteh-Bakht SC, Obach RS, O’Donnell JP. Chem. Res. Toxicol. 2002; 15: 269
- 1e Boeini HZ, Najafabadi KH. Eur. J. Org. Chem. 2009; 4926
- 2a Riadi Y, Mamouni R, Azzalou R, El Haddad M, Routier S, Guillaumet G, Lazar S. Tetrahedron Lett. 2011; 52: 3492
- 2b Wang H, Wang L, Shang J, Li X, Wang H, Gui J, Lei A. Chem. Commun. 2012; 48: 76
- 2c Bonnamour J, Bolm C. Org. Lett. 2008; 10: 2665
- 2d Yuan Y, Thomé I, Kim SH, Chen D, Beyer A, Bonnamour J, Zuidema E, Chang S, Bolm C. Adv. Synth. Catal. 2010; 352: 2892
- 3 Lee D.-H, Choi M, Yu B.-W, Ryoo R, Taher A, Hossain S, Jin M.-J. Adv. Synth. Catal. 2009; 351: 2912
- 4a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 4b Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
- 5 Shibahara F, Yamaguchi E, Murai T. Chem. Commun. 2010; 46: 2471
- 6 Huang J, Chan J, Chen Y, Borths CJ, Baucom KD, Larsen RD, Faul MM. J. Am. Chem. Soc. 2010; 132: 3674
- 7 Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2007; 129: 12404
- 8 Sezen B, Sames D. Org. Lett. 2003; 5: 3607
- 9 Zhang W, Zeng Q, Zhang X, Tian Y, Yue Y, Guo Y, Wang Z. J. Org. Chem. 2011; 76: 4741
- 10 Guchhait SK, Kashyap M, Saraf S. Synthesis 2010; 1166
- 11 Hachiya H, Hirano K, Satoh T, Miura M. ChemCatChem 2010; 2: 1403
- 12 Ranjit S, Liu X. Chem. Eur. J. 2011; 17: 1105
- 13 Wang H, Wang Y, Peng C, Zhang J, Zhu Q. J. Am. Chem. Soc. 2010; 132: 13217
- 14 Li Z, Cui Z, Liu Z.-Q. Org. Lett. 2013; 15: 406
- 15 Yang F, Xu Z, Wang Z, Yu Z, Wang R. Chem. Eur. J. 2011; 17: 6321
- 16 Liu X, Zhang S. Synlett 2011; 268
- 17 Liu X, Zhang S. Synlett 2011; 1137
- 18 Zhang S, Liu X, Wang T. Adv. Synth. Catal. 2011; 353: 1463
- 19 Wang P, Liu X, Zhang S. Chin. J. Chem. 2013; 31: 187
- 20a King AE, Brunold TC, Stahl SS. J. Am. Chem. Soc. 2009; 131: 5044
- 20b Ribas X, Calle C, Poater A, Casitas A, Gómez L, Xifra R, Parella T, Benet-Buchholz J, Schweiger A, Mitrikas G, Solà M, Llobet A, Stack TD. P. J. Am. Chem. Soc. 2010; 132: 12299
- 20c Casitas A, King AE, Parella T, Costas M, Stahl SS, Ribas X. Chem. Sci. 2010; 1: 326
- 21 Ackermann L, Althammer A, Fenner S. Angew. Chem. Int. Ed. 2009; 48: 201
- 22 Ackermann L, Barfüsser S, Pospech J. Org. Lett. 2010; 12: 724
- 23 Blacker AJ, Farah MM, Hall MI, Marsden SP, Saidi O, Williams JM. J. Org. Lett. 2009; 11: 2039
- 24 Xing R.-G, Li Y.-N, Liu Q, Meng Q.-Y, Li J, Shen X.-X, Liu Z, Zhou B, Yao X, Liu Z.-L. Eur. J. Org. Chem. 2010; 6627
- 25 Hachiya H, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 1737
- 26 Bayh O, Awad H, Mongin F, Hoarau C, Bischoff L, Trécourt F, Quéguiner G, Marsais F, Blanco F, Abarca B, Ballesteros R. J. Org. Chem. 2005; 70: 5190
- 27 Laroche J, Beydoun K, Guerchais V, Doucet H. Catal. Sci. Technol. 2013; 3: 2072
- 28 Lee JJ, Kim J, Jun YM, Lee BM, Kim BH. Tetrahedron 2009; 65: 8821
- 29 Zhang M, Zhang S, Liu M, Cheng J. Chem. Commun. 2011; 47: 11522
- 30 Flegeau EF, Popkin ME, Greaney MF. Org. Lett. 2006; 8: 2495
- 31 Saha D, Adak L, Ranu BC. Tetrahedron Lett. 2010; 51: 5624
- 32 Inamoto K, Hasegawa C, Hiroya K, Doi T. Org. Lett. 2008; 10: 5147
- 33 Yamamoto T, Muto K, Komiyama M, Canivet J, Yamaguchi J, Itami K. Chem. Eur. J. 2011; 17: 10113