A Highly Efficient Copper-Catalyzed Method for the Synthesis of 2-Hydroxybenzamides in Water

Shah Jaimin Balkrishna; Sangit Kumar

doi:10.1055/s-0031-1289755

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(9): 1417-1426
DOI: 10.1055/s-0031-1289755

paper

A Highly Efficient Copper-Catalyzed Method for the Synthesis of 2-Hydroxybenzamides in Water

Autoren

Shah Jaimin Balkrishna

Department of Chemistry, Indian Institute of Science Education and Research (IISER), Bhopal 462023, MP, India , Fax: +91(755)409 2392 eMail: SangitKumar@iiserbhopal.ac.in
Sangit Kumar*

Department of Chemistry, Indian Institute of Science Education and Research (IISER), Bhopal 462023, MP, India , Fax: +91(755)409 2392 eMail: SangitKumar@iiserbhopal.ac.in

Abstract

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Abstract

An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33–96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides.

Key words

copper - 2-hydroxybenzamides - hydroxylation - catalysis in water - C–O coupling

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Referenzen

References

1a Zhang J, Tang Y, Tang N, Tan M.-Y, Liu W.-S, Yu K.-B. J. Chem. Soc., Dalton Trans. 2002; 832
1b Guo L, Wang Q.-L, Jiang Q.-Q, Jiang Q.-J, Jiang Y.-B. J. Org. Chem. 2007; 72: 9947
1c Yan X, Cai Z, Yi C, Liu W, Tan M, Tang Y. Inorg. Chem. 2011; 50: 2346

2a Hoveyda HR, Karunaratne V, Rettig SJ, Orvig C. Inorg. Chem. 1992; 31: 5408
2b Pirrung MC, Tumey LN. J. Comb. Chem. 2000; 2: 675

3a Kumar A, Narasimhan B, Kumar D. Bioorg. Med. Chem. 2007; 15: 4113
3b Cheng K, Zheng Q.-Z, Qian Y, Shi L, Zhao J, Zhu H.-L. Bioorg. Med. Chem. 2009; 17: 7861
3c Rordíguez-Rodríguez C, de Groot NS, Rimola A, Álvarez-Larena Á, Lloveras V, Vidal-Gancedo J, Ventura S, Vendrell J, Sodupe M, Gonsález-Duarte P. J. Am. Chem. Soc. 2009; 131: 1436
3d Imramovsky A, Pesko M, Kralova K, Vejsova M, Stolarikova J, Vinsova J, Jampilek J. Molecules 2011; 16: 2414

4a Liechti C, Sequin U, Bold G, Furet P, Meyer T, Traxler P. Eur. J. Med. Chem. 2004; 39: 11
4b Kamatb S, Buolamwini JK. Med. Res. Rev. 2006; 26: 569

5 Marzi E, Gorecka J, Schlosser M. Synthesis 2004; 1609

See references on C–N coupling reactions:
6a Antilla JC, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 11684
6b Klapars A, Huang X, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 7421
6c Cristau HJ, Cellier PP, Spindler JF, Taillefer M. Chem.–Eur. J. 2004; 10: 5607
6d Oshovsky GV, Ouali A, Xia N, Zablocka M, Boeré RT, Taillefer M, Ouali A, Renard B, Spindler J.-F. Chem.–Eur. J. 2006; 12: 5301
6e Taillefer M, Xia N, Ouali A. Angew. Chem. Int. Ed. 2007; 46: 934 ; Angew Chem. 2007, 119, 952
6f Zhu L, Cheng L, Zhang Y, Xie R, You J. J. Org. Chem. 2007; 72: 2737
6g Zhu L, Guo P, Li G, Lan J, Xie R, You J. J. Org. Chem. 2007; 72: 8535
6h Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2008; 47: 3096 ; Angew. Chem. 2008, 120, 3140
6i Kaddouri H, Vicente V, Ouali A, Ouazzani F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 333 ; Angew. Chem. 2009, 121, 339
6j Xia N, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 337 ; Angew. Chem. 2009, 121, 343
6k Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954 ; Angew. Chem. 2009, 121, 7088
6l Racine E, Monnier F, Vors J.-P, Taillefer M. Org. Lett. 2011; 13: 2818
6m Cristau H.-J, Cellier PP, Spindler J.-F, Taillefer M. Eur. J. Org. Chem. 2004; 695

See references on C-heteroatom (N/O/S/S/Te) coupling reactions:
7a Taniguchi N, Onami T. J. Org. Chem. 2004; 69: 915
7b Kumar S, Engman L. J. Org. Chem. 2006; 71: 5400
7c Ouali A, Laurent R, Caminade A.-M, Majoral J.-P, Taillefer M. J. Am. Chem. Soc. 2006; 128: 15990
7d Ouali A, Spindler J.-F, Cristau H.-J, Taillefer M. Adv. Synth. Catal. 2006; 348: 499
7e Ouali A, Spindler J.-F, Jutand A, Taillefer M. Adv. Synth. Catal. 2007; 349: 1906
7f Xia N, Taillefer M. Chem.–Eur. J. 2008; 14: 6037
7g Benyahya S, Monnier F, Taillefer M, Man MW. C, Bied C, Ouazzani F. Adv. Synth. Catal. 2008; 350: 2205
7h Benyahya S, Monnier F, Man MW. C, Bied C, Ouazzani F, Taillefer M. Green Chem. 2009; 11: 1121
7i Zhu L, Li G, Luo L, Guo P, Lan J, You J. J. Org. Chem. 2009; 74: 2200
7j Tlili A, Monnier F, Taillefer M. Chem.–Eur. J. 2010; 16: 12299
7k Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
7l Cristau H.-J, Cellier PP, Hamada S, Spindler J.-F, Taillefer M. Org. Lett. 2004; 6: 913
7m Taillefer M, Cristau H.-J, Cellier PP, Spindler J.-F. French Patent FR 16547, 2001
7n Taillefer M, Cristau H.-J, Cellier PP, Spindler J.-F. US Patent 10/159506 (US 030171593), 2002
7o Taillefer M, Cristau H.-J, Cellier PP, Spindler J.-F. US 10/159829 (US 030236413), 2002
7p Taillefer M, Cristau H.-J, Cellier PP, Spindler J.-F, Ouali A. French Patent FR 6717 (WO 031101966), 2002

8a Taillefer M, Tlili A, Monnier F, Xia N. French Patent FR 02767 (WO 2010/142913 A1), 2009
8b Tlili A, Xia N, Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 8725 ; Angew Chem. 2009, 121, 8881

9a Zhao D, Wu N, Zhang S, Xi P, Su X, Lan J, You J. Angew. Chem. Int. Ed. 2009; 48: 8729 ; Angew. Chem. 2009, 121, 8885
9b Jing L, Wei J, Zhou L, Huang Z, Lia Z, Zhou X. Chem. Commun. 2010; 46: 4767
9c Yang D, Fu H. Chem.–Eur. J. 2010; 16: 2366
9d Maurer S, Liu W, Zhang X, Jiang Y, Ma D. Synlett 2010; 976
9e Xu J, Wang X, Shao C, Su D, Cheng G, Hu Y. Org. Lett. 2010; 12: 1964
9f Thakur KG, Sekar G. Chem. Commun. 2011; 47: 6692
9g Yang K, Li Z, Wang Z, Yao Z, Jiang S. Org. Lett. 2011; 13: 4340
9h Inamoto K, Nozawa K, Yonemoto M, Kondo Y. Chem. Commun. 2011; 47: 11775

10 Xu H.-J, Liang Y.-F, Cai Z.-Y, Qi H.-X, Yang C.-Y, Feng Y.-S. J. Org. Chem. 2011; 76: 2296

11a Yang K, Qiu Y, Li Z, Wang Z, Jiang S. J. Org. Chem. 2011; 76: 3151
11b Qiu Y, Liu Y, Yang K, Hong W, Li Z, Wang Z, Jiang S. Org. Lett. 2011; 13: 3556
11c Rao H, Jin Y, Fu H, Jiang Y, Zhao Y. Chem.–Eur. J. 2006; 12: 3636
11d Chen Y, Chen H. Org. Lett. 2006; 8: 5609
11e Lv X, Bao W. J. Org. Chem. 2007; 72: 3863
11f Zhao Y, Wang Y, Sun H, Li L, Zhang H. Chem Commun. 2007; 3186
11g Niu J, Zhou H, Li Z, Xu J, Hu S. J. Org. Chem. 2008; 73: 7814
11h Zhang J, Zhang Z, Wang Y, Zheng X, Wang Z. Eur. J. Org. Chem. 2008; 5112
11i Naidu AB, Raghunath OR, Prasad DJ. C, Sekar G. Tetrahedron Lett. 2008; 49: 1057

12a Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB. Angew. Chem. Int. Ed. 2005; 44: 3275 ; Angew. Chem. 2005, 117, 3339
12b Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68

See references on copper-catalyzed reactions in water:
13a Carril M, Martin RS, Tellitu I, Dominguez E. Org. Lett. 2006; 8: 1467
13b Carril M, Martin RS, Domenguez E, Tellitu I. Chem.–Eur. J. 2007; 13: 5100
13c Wu Z, Jiang Z, Wu D, Xiang H, Zhou X. Eur. J. Org. Chem. 2010; 1854
13d Wu Z, Huang Q, Zhou X, Yu L, Li Z, Wu D. Eur. J. Org. Chem. 2011; 5242
13e Wang Y, Wu Z, Wang L, Li Z, Zhou X. Chem.–Eur. J. 2009; 15: 8971
13f Liang L, Li Z, Zhou X. Org. Lett. 2009; 11: 3294
13g Qu Y, Ke F, Zhou L, Li Z, Xiang H, Wu D, Zhou X. Chem. Commun. 2010; 46: 4767
13h Ke F, Qu Y, Jiang Z, Li Z, Wu D, Zhou X. Org. Lett. 2011; 13: 454

14a Balkrishna SJ, Bhakuni BS, Chopra D, Kumar S. Org. Lett. 2010; 12: 5394
14b Balkrishna SJ, Bhakuni BS, Kumar S. Tetrahedron 2011; 67: 9565

15a Nakajima M, Miyoshi I, Kanayama K, Hashimoto S.-I, Noji M, Koga K. J. Org. Chem. 1999; 64: 2264
15b Habaue S, Takahashi Y, Temma T. Tetrahedron Lett. 2007; 48: 7301

For references on pyridinols, see:
16a Kumar S, Johansson H, Kanda T, Engman L, Müller T, Jonsson M, Pedulli GF, Petrucci S, Valgimigli L. Org. Lett. 2008; 10: 4895
16b Kumar S, Johansson H, Kanda T, Engman L, Müller T, Bergenudd H, Jonsson M, Pedulli GF, Amorati R, Valgimigli L. J. Org. Chem. 2010; 75: 716 ; and references cited therein

17a Cheng K, Zheng Q.-Z, Qian Y, Shi L, Zhao J, Zhu H.-L. Bioorg. Med. Chem. 2009; 17: 7861
17b Liu D, Tang K, Liu W, Su C, Yan X, Tan M, Tang Y. Dalton Trans. 2010; 39: 9763

18 Zhang S.-L, Liu L, Fu Y, Guo Q.-X. Organometallics 2007; 26: 4546
19 This result is consistent with our observation on copper-catalyzed Se–N coupling reaction in which 2-halo-N-benzylbenzamide smoothly yielded corresponding isoselenazolone whereas 2-halobenzoic acid failed to provide any selenated product
20 Dermer OC, King J. J. Org. Chem. 1943; 8: 168
21 Black M, Cadagon JI. G, McNab H. J. Chem. Soc., Perkin Trans. 1 1994; 155
22 Paris GY, Chambers CH. J. Med. Chem. 1966; 9: 971
23 Dickie JP, Loomans ME, Farley TM, Strong FM. J. Med. Chem. 1963; 6: 424
24 Phillips AP, Baltzly R. J. Am. Chem. Soc. 1947; 69: 200
25 Ruschig H, Soden B, Korger G, Nesemann G. US Patent 2923737, 1960
26 Cheng K, Zheng Q.-Z, Qian Y, Shi L, Zhao J, Zhu H.-L. Bioorg. Med. Chem. 2009; 17: 7861
27 Malhas RN, Ibrahim YA. Synthesis 2006; 3261

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