SCOPUS 정보 검색 플랫폼

Volumn 1, Issue 2, 2011, Pages 234-238

Sulfonic acid containing cation-exchanger resin "iNDION-770" and copper(i) salts: A novel reusable catalyst for N-arylation of NH-heterocycles with haloarenes

(4) Amal Joseph, P J a Priyadarshini, S a Lakshmi Kantam, M a Maheswaran, H a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATION EXCHANGERS; HALOARENES; HETEROCYCLES; HETEROGENEOUS CATALYTIC SYSTEMS; N-ARYLATIONS; REUSABLE CATALYSTS; SULFONIC ACID;

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; ION EXCHANGERS; POSITIVE IONS; RESINS;

SALTS;

EID: 79955406817 PISSN: 20444753 EISSN: 20444761 Source Type: Journal
DOI: 10.1039/c0cy00074d Document Type: Article

Times cited : (20)

References (57)

1
- 0000076248
- A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1st edn, Ed.
- J. Elguero, in Comprehensive Heterocyclic Chemistry, ed., A. R. Katritzky, and, C. W. Rees, Pergamon Press, Oxford, 1st edn, 1984, vol. 5, p. 291
- (1984) Comprehensive Heterocyclic Chemistry , pp. 291
- Elguero, J.¹

2
- 0003030373
- A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Elsevier Science Ltd., Oxford, 1st edn, Ed.
- J. Elguero, in Comprehensive Heterocyclic Chemistry II, ed., A. R. Katritzky, C. W. Rees, and, E. F. V. Scriven, Pergamon, Elsevier Science Ltd., Oxford, 1st edn, 1996, vol. 3, p. 70
- (1996) Comprehensive Heterocyclic Chemistry II , pp. 70
- Elguero, J.¹

3
- 20144374942
- M. L. Quan P. Y. S. Lam Q. Han D. J. P. Pinto M. Y. He R. Li C. D. Ellis C. G. Clark C. A. Teleha J. H. Sun R. S. Alexander S. Bai J. M. Luettgen R. M. Knabb P. C. Wong P. R. R. Wexler J. Med. Chem. 2005 48 1729
- (2005) J. Med. Chem. , vol.48 , pp. 1729
- Quan, M.L.¹ Lam, P.Y.S.² Han, Q.³ Pinto, D.J.P.⁴ He, M.Y.⁵ Li, R.⁶ Ellis, C.D.⁷ Clark, C.G.⁸ Teleha, C.A.⁹ Sun, J.H.¹⁰ Alexander, R.S.¹¹ Bai, S.¹² Luettgen, J.M.¹³ Knabb, R.M.¹⁴ Wong, P.C.¹⁵ Wexler, P.R.R.¹⁶

4
- 1242294357
- B. Dyck V. S. Goodfellow T. Phillips J. Grey M. Haddach M. Rowbottom G. S. Naeve B. Brown Saunders Bioorg. Med. Chem. Lett. 2004 14 1151
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 1151
- Dyck, B.¹ Goodfellow, V.S.² Phillips, T.³ Grey, J.⁴ Haddach, M.⁵ Rowbottom, M.⁶ Naeve, G.S.⁷ Brown, B.⁸ Saunders⁹

5
- 0003780442
- C. J. Drayton, Pergamon, New York, NY
- P. N. Craig, in Comprehensive Medicinal Chemistry, ed., C. J. Drayton, Pergamon, New York, NY, 1991, vol. 8
- (1991) Comprehensive Medicinal Chemistry, Ed.
- Craig In, P.N.¹

6
- 67649337286
- N. R. Candeias L. C. Branco P. M. Gois C. A. M. Afonso A. F. Trindade Chem. Rev. 2009 109 2703
- (2009) Chem. Rev. , vol.109 , pp. 2703
- Candeias, N.R.¹ Branco, L.C.² Gois, P.M.³ Afonso, C.A.M.⁴ Trindade, A.F.⁵

7
- 0033515805
- A. Kiyomori J. F. Marcoux S. L. Buchwald Tetrahedron Lett. 1999 40 2657
- (1999) Tetrahedron Lett. , vol.40 , pp. 2657
- Kiyomori, A.¹ Marcoux, J.F.² Buchwald, S.L.³

8
- 0037009958
- J. C. Antilla A. Klapars S. L. Buchwald J. Am. Chem. Soc. 2002 124 11684
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 11684
- Antilla, J.C.¹ Klapars, A.² Buchwald, S.L.³

9
- 4143104684
- J. C. Antilla J. M. Baskin T. E. Barder S. L. Buchwald J. Org. Chem. 2004 69 5578
- (2004) J. Org. Chem. , vol.69 , pp. 5578
- Antilla, J.C.¹ Baskin, J.M.² Barder, T.E.³ Buchwald, S.L.⁴

10
- 1642479421
- H.-J. Cristau P. P. Cellier J.-F. Spindler M. Taillefer Eur. J. Org. Chem. 2004 695
- (2004) Eur. J. Org. Chem. , pp. 695
- Cristau, H.-J.¹ Cellier, P.P.² Spindler, J.-F.³ Taillefer, M.⁴

11
- 9244225109
- H.-J. Cristau P. P. Cellier J.-F. Spindler M. Taillefer Chem.-Eur. J. 2004 10 5607
- (2004) Chem.-Eur. J. , vol.10 , pp. 5607
- Cristau, H.-J.¹ Cellier, P.P.² Spindler, J.-F.³ Taillefer, M.⁴

12
- 20844435969
- D. Ma Q. Cai H. Zhang J. Org. Chem. 2005 70 5164
- (2005) J. Org. Chem. , vol.70 , pp. 5164
- Ma, D.¹ Cai, Q.² Zhang, H.³

13
- 28044443893
- L. Liu M. Frohn N. Xi D. Celia H. Randy P. J. Reider J. Org. Chem. 2005 70 10135
- (2005) J. Org. Chem. , vol.70 , pp. 10135
- Liu, L.¹ Frohn, M.² Xi, N.³ Celia, D.⁴ Randy, H.⁵ Reider, P.J.⁶

14
- 33746174994
- R. A. Altman S. L. Buchwald Org. Lett. 2006 8 2779
- (2006) Org. Lett. , vol.8 , pp. 2779
- Altman, R.A.¹ Buchwald, S.L.²

15
- 34547636188
- R. A. Altman E. D. Koval S. L. Buchwald J. Org. Chem. 2007 72 6190
- (2007) J. Org. Chem. , vol.72 , pp. 6190
- Altman, R.A.¹ Koval, E.D.² Buchwald, S.L.³

16
- 38449099744
- R. A. Altman S. L. Buchwald Nat. Protoc. 2007 2 2474
- (2007) Nat. Protoc. , vol.2 , pp. 2474
- Altman, R.A.¹ Buchwald, S.L.²

17
- 34247232757
- L. Zhu L. Cheng Y. Zhang R. Xie J. You J. Org. Chem. 2007 72 2737
- (2007) J. Org. Chem. , vol.72 , pp. 2737
- Zhu, L.¹ Cheng, L.² Zhang, Y.³ Xie, R.⁴ You, J.⁵

18
- 34248588689
- L.-V. Xin W. Bao J. Org. Chem. 2007 72 3863
- (2007) J. Org. Chem. , vol.72 , pp. 3863
- Xin, L.-V.¹ Bao, W.²

19
- 33750499990
- X. Guo H. Rao Y. Fu Y. Jiang Y. Zhao Adv. Synth. Catal. 2006 348 2197
- (2006) Adv. Synth. Catal. , vol.348 , pp. 2197
- Guo, X.¹ Rao, H.² Fu, Y.³ Jiang, Y.⁴ Zhao, Y.⁵

20
- 38649086071
- H. Maheswaran G. G. Krishna K. L. Prasanth V. Srinivas G. K. Chaitanya K. Bhanuprakash Tetrahedron 2008 64 2471
- (2008) Tetrahedron , vol.64 , pp. 2471
- Maheswaran, H.¹ Krishna, G.G.² Prasanth, K.L.³ Srinivas, V.⁴ Chaitanya, G.K.⁵ Bhanuprakash, K.⁶

21
- 79958153937
- F. W. Li T. S. A. Hor Chem.-Eur. J. 2009 15 10585
- (2009) Chem.-Eur. J. , vol.15 , pp. 10585
- Li, F.W.¹ Hor, T.S.A.²

22
- 70349929617
- For copper(II) catalyzed N-arylation of imidazole, see:
- P. F. Larsson A. Correa M. Carril P. O. Norrby C. Bolm Angew. Chem., Int. Ed. 2009 48 5691
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5691
- Larsson, P.F.¹ Correa, A.² Carril, M.³ Norrby, P.O.⁴ Bolm, C.⁵

23
- 70349146722
- For reviews, see:
- Y. Wang Z. Wu L. Wang Z. Li X. Zhou Chem.-Eur. J. 2009 15 8971
- (2009) Chem.-Eur. J. , vol.15 , pp. 8971
- Wang, Y.¹ Wu, Z.² Wang, L.³ Li, Z.⁴ Zhou, X.⁵

24
- 0345708168
- S. V. Ley A. W. Thomas Angew. Chem., Int. Ed. 2003 42 5400
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5400
- Ley, S.V.¹ Thomas, A.W.²

25
- 33747071481
- J.-P. Corbet G. Mignani Chem. Rev. 2006 106 2651
- (2006) Chem. Rev. , vol.106 , pp. 2651
- Corbet, J.-P.¹ Mignani, G.²

26
- 51049095122
- G. Evano N. Blanchard M. Toumi Chem. Rev. 2008 108 3054
- (2008) Chem. Rev. , vol.108 , pp. 3054
- Evano, G.¹ Blanchard, N.² Toumi, M.³

27
- 70349786460
- The palladium based catalysts have also been shown to be useful for N-arylation reactions, for references, see:
- F. Monnier M. Taillefer Angew. Chem., Int. Ed. 2009 48 6954
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 6954
- Monnier, F.¹ Taillefer, M.²

28
- 0033549829
- J. P. Wolfe S. L. Buchwald Angew. Chem., Int. Ed. 1999 38 2413
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2413
- Wolfe, J.P.¹ Buchwald, S.L.²

29
- 0000157513
- A. R. Muci S. L. Buchwald Top. Curr. Chem. 2002 219 131
- (2002) Top. Curr. Chem. , vol.219 , pp. 131
- Muci, A.R.¹ Buchwald, S.L.²

30
- 0242563114
- A. Didier, Wiley-VCH, Weinheim, Ed.
- J. F. Hartwig, in Modern Arene Chemistry, ed., A. Didier, Wiley-VCH, Weinheim, 2002, p. 107
- (2002) Modern Arene Chemistry , pp. 107
- Hartwig, J.F.¹

31
- 0346749657
- K. Kunz U. Scholz D. Ganzer Synlett 2003 2428
- (2003) Synlett , pp. 2428
- Kunz, K.¹ Scholz, U.² Ganzer, D.³

32
- 12344337315
- B. Schlummer U. Scholz Adv. Synth. Catal. 2004 346 1599
- (2004) Adv. Synth. Catal. , vol.346 , pp. 1599
- Schlummer, B.¹ Scholz, U.²

33
- 70350132020
- H. Xu Mini-Rev. Org. Chem. 2009 6 367
- (2009) Mini-Rev. Org. Chem. , vol.6 , pp. 367
- Xu, H.¹

34
- 78449260529
- Recently iron based catalysts were used for N-arylation of NH-heterocycles. For references, see:
- B. P. Fors S. L. Buchwald J. Am. Chem. Soc. 2010 132 15914
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 15914
- Fors, B.P.¹ Buchwald, S.L.²

35
- 36749002068
- A. Correa C. Bolm Angew. Chem., Int. Ed. 2007 46 8862
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 8862
- Correa, A.¹ Bolm, C.²

36
- 44349100663
- A. Correa C. Bolm Adv. Synth. Catal. 2008 350 391
- (2008) Adv. Synth. Catal. , vol.350 , pp. 391
- Correa, A.¹ Bolm, C.²

37
- 63349110330
- Y. C. Teo Adv. Synth. Catal. 2009 351 720
- (2009) Adv. Synth. Catal. , vol.351 , pp. 720
- Teo, Y.C.¹

38
- 22244438188
- B. M. Choudary C. Sridhar M. L. Kantam G. T. Venkanna B. Sreedhar J. Am. Chem. Soc. 2005 127 9948
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 9948
- Choudary, B.M.¹ Sridhar, C.² Kantam, M.L.³ Venkanna, G.T.⁴ Sreedhar, B.⁵

39
- 69749096440
- B. Sreedhar R. Arundhathi P. L. Reddy M. A. Reddy M. L. Kantam Synthesis 2009 2517
- (2009) Synthesis , pp. 2517
- Sreedhar, B.¹ Arundhathi, R.² Reddy, P.L.³ Reddy, M.A.⁴ Kantam, M.L.⁵

40
- 70349868159
- The industrial grade cation exchanger INDION-770 resin is readily available in low price from Ion-Exchange India Limited. More detailed specifications for the INDION-770 resin can be obtained from the website For rate enhancements with copper carboxylates in "living" radical polymerization reactions, see:
- B. Sreedhar R. Arundhathi P. L. Reddy M. L. Kantam J. Org. Chem. 2009 74 7951
- (2009) J. Org. Chem. , vol.74 , pp. 7951
- Sreedhar, B.¹ Arundhathi, R.² Reddy, P.L.³ Kantam, M.L.⁴

41
- 0032315134
- M. van der Sluis B. Barboiu N. Pesa V. Percec Macromolecules 1998 31 9409
- (1998) Macromolecules , vol.31 , pp. 9409
- Van Der Sluis, M.¹ Barboiu, B.² Pesa, N.³ Percec, V.⁴

42
- 0031118574
- In copper(i)-catalyzed Ullmann-type cross-coupling reactions, positive rate enhancement with respect to unfunctionalized substrates has been demonstrated using coupling partners that contain a copper-chelating carboxylic group, such as 2-halogenobenzoic acids, α-amino acids, and β-amino acids, in the reactions, see:
- M. Wei J. Xia S. G. Gaynor K. Matyjaszewski Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1997 38 685
- (1997) Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) , vol.38 , pp. 685
- Wei, M.¹ Xia, J.² Gaynor, S.G.³ Matyjaszewski, K.⁴

43
- 0001559708
- C. Couture A. J. Paine Can. J. Chem. 1985 63 111
- (1985) Can. J. Chem. , vol.63 , pp. 111
- Couture, C.¹ Paine, A.J.²

44
- 0346749657
- K. Kunz U. Scholz D. Ganzer Synlett 2003 2428
- (2003) Synlett , pp. 2428
- Kunz, K.¹ Scholz, U.² Ganzer, D.³

45
- 21344443884
- Z. Wang W. Bao Y. Jiang Chem. Commun. 2005 2849
- (2005) Chem. Commun. , pp. 2849
- Wang, Z.¹ Bao, W.² Jiang, Y.³

46
- 57549098954
- See also ref. 3e
- D. Ma Q. Cai Acc. Chem. Res. 2008 41 1450
- (2008) Acc. Chem. Res. , vol.41 , pp. 1450
- Ma, D.¹ Cai, Q.²

47
- 58149284026
- H. Maheswaran G. G. Krishna V. Srinivas K. L. Prasanth C. V. Rajasekhar Bull. Chem. Soc. Jpn. 2008 81 515
- (2008) Bull. Chem. Soc. Jpn. , vol.81 , pp. 515
- Maheswaran, H.¹ Krishna, G.G.² Srinivas, V.³ Prasanth, K.L.⁴ Rajasekhar, C.V.⁵

48
- 0029979566
- G. D. Allred L. S. Liebeskind J. Am. Chem. Soc. 1996 118 2748
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 2748
- Allred, G.D.¹ Liebeskind, L.S.²

49
- 0000139143
- For a review on various uses of CuTC, see:
- S. Zhang D. Zhang L. S. Liebeskind J. Org. Chem. 1997 62 2312
- (1997) J. Org. Chem. , vol.62 , pp. 2312
- Zhang, S.¹ Zhang, D.² Liebeskind, L.S.³

50
- 25444482838
- A. Innitzer Synlett 2005 2405
- (2005) Synlett , pp. 2405
- Innitzer, A.¹

51
- 0035843313
- C. Savarin J. Srogl L. S. Liebeskind Org. Lett. 2001 3 91
- (2001) Org. Lett. , vol.3 , pp. 91
- Savarin, C.¹ Srogl, J.² Liebeskind, L.S.³

52
- 0034669524
- Recently 'catechol violet' was used as an additive in Cu(i) catalyzed direct C-S bond forming reactions of haloarenes. Notably, catechol violet contains the sulfonic acid group, for reference, see:
- L. S. Liebeskind J. Srogl J. Am. Chem. Soc. 2000 122 11260
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 11260
- Liebeskind, L.S.¹ Srogl, J.²

53
- 68349152518
- a values of NH-hydrogens in benzimidazole, imidazole and pyrazole in DMSO are 16.4, 18.6 and 19.8 respectively. This shows that imidazole NH-hydrogen is more acidic than those in pyrazole. For reference, see:
- B. Basu B. Mandal S. Das S. Kundu Tetrahedron Lett. 2009 50 5523
- (2009) Tetrahedron Lett. , vol.50 , pp. 5523
- Basu, B.¹ Mandal, B.² Das, S.³ Kundu, S.⁴

54
- 0344887064
- The copper exchanged INDION-770 resin (both fresh and recycled catalyst) has been characterized by XPS and SEM studies. For more details, see ESI
- F. G. Bordwell Acc. Chem. Res. 1988 21 456
- (1988) Acc. Chem. Res. , vol.21 , pp. 456
- Bordwell, F.G.¹

55
- 62649152953
- E. R. Strieter B. Bhayana S. L. Buchwald J. Am. Chem. Soc. 2009 131 78
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 78
- Strieter, E.R.¹ Bhayana, B.² Buchwald, S.L.³

56
- 77951699144
- G. O. Jones P. Liu K. N. Houk S. L. Buchwald J. Am. Chem. Soc. 2010 132 6205
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 6205
- Jones, G.O.¹ Liu, P.² Houk, K.N.³ Buchwald, S.L.⁴

57
- 0003412412
- John Wiley and Sons, 6th edn, p. 854 It is well-known and also our experimental observation that for highly activated nitro groups containing haloarenes such as 4-iodonitrobenzene or 4-bromonitrobenzene, the cross-coupling reactions with nucleophiles proceed in the absence of any catalysts under the likely influence of SNAr pathways SNAr pathways do not require any catalyst to promote the reaction; for reference to SNAr pathways
- SNAr pathways do not require any catalyst to promote the reaction; for reference to SNAr pathways see: M. B. Smith and J. March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, John Wiley and Sons, 6th edn, 2007, p. 854
- (2007) March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
- Smith, M.B.¹ March, J.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.