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Advanced Synthesis and Catalysis

Volumn 352, Issue 11-12, 2010, Pages 2041-2049

Direct synthesis of pyrazolo[5,1-a]isoindoles via intramolecular palladium-catalyzed C-H bond activation

(5) Choi, Young Lok a,b Lee, Hyuk a Kim, Bum Tae a Choi, Kihang b Heo, Jung Nyoung a

a Korea Research Institute of Chemical Technology (South Korea)

b Korea University (South Korea)

Author keywords

C H activation; Direct arylation; Palladium; Pyrazoles

Indexed keywords

EID: 77956378879 PISSN: 16154150 EISSN: 16154169 Source Type: Journal
DOI: 10.1002/adsc.201000260 Document Type: Article

Times cited : (32)

References (63)

1
- 69249101991
- a) G. P. McGlacken, L. M. Bateman, Chem. Soc. Rev. 2009, 38, 2447-2464
- (2009) Chem. Soc. Rev. , vol.38 , pp. 2447-2464
- McGlacken, G.P.¹ Bateman, L.M.²

2
- 77949410036
- b) L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976-10011
- (2009) Angew. Chem. , vol.121 , pp. 9976-10011
- Ackermann, L.¹ Vicente, R.² Kapdi, A.R.³

3
- 72449170089
- Angew. Chem. Int. Ed. 2009, 48, 9792-9826
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9792-9826

4
- 68949185025
- c) O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074-1086
- (2009) Acc. Chem. Res. , vol.42 , pp. 1074-1086
- Daugulis, O.¹ Do, H.-Q.² Shabashov, D.³

5
- 71949100273
- d) X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196-5217
- (2009) Angew. Chem. , vol.121 , pp. 5196-5217
- Chen, X.¹ Engle, K.M.² Wang, D.-H.³ Yu, J.-Q.⁴

6
- 67649488045
- Angew. Chem. Int. Ed. 2009, 48, 5094-5115
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5094-5115

7
- 51649122191
- e) J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013-1025
- (2008) Acc. Chem. Res. , vol.41 , pp. 1013-1025
- Lewis, J.C.¹ Bergman, R.G.² Ellman, J.A.³

8
- 42949122199
- f) B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 949-957
- (2008) Synlett , pp. 949-957
- Li, B.-J.¹ Yang, S.-D.² Shi, Z.-J.³

9
- 33947727055
- g) R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874-922
- (2007) Chem. Rev. , vol.107 , pp. 874-922
- Chinchilla, R.¹ Nájera, C.²

10
- 33846918696
- h) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238
- (2007) Chem. Rev. , vol.107 , pp. 174-238
- Alberico, D.¹ Scott, M.E.² Lautens, M.³

11
- 34248361209
- i) L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35-41
- (2007) Aldrichimica Acta , vol.40 , pp. 35-41
- Campeau, L.-C.¹ Stuart, D.R.² Fagnou, K.³

12
- 33645674829
- j) K. Godula, D. Sames, Science 2006, 312, 67-72.
- (2006) Science , vol.312 , pp. 67-72
- Godula, K.¹ Sames, D.²

13
- 77956384657
- For selected recent examples of Pd(0)-catalyzed C-H activation with aryl (peudo)halides, see: a) M. Wasa, B. T. Worrell, J.-Q. Yu, Angew. Chem. 2010, 122, 1297-1299
- (2010) Angew. Chem. , vol.122 , pp. 1297-1299
- Wasa, M.¹ Worrell, B.T.² Yu, J.-Q.³

14
- 76349089782
- Angew. Chem. Int. Ed. 2010, 49, 1275-1277
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1275-1277

15
- 74849095513
- b) T. Nishikata, A. R. Abela, B. H. Lipshutz, Angew. Chem. Int. Ed. 2010, 49, 781-784
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 781-784
- Nishikata, T.¹ Abela, A.R.² Lipshutz, B.H.³

16
- 70349900133
- c) L. Ackermann, A. Althammer, S. Fenner, Angew. Chem. 2009, 121, 207-210
- (2009) Angew. Chem. , vol.121 , pp. 207-210
- Ackermann, L.¹ Althammer, A.² Fenner, S.³

17
- 58249118877
- Angew. Chem. Int. Ed. 2009, 48, 201-204
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 201-204

18
- 67749129343
- d) L.-C. Campeau, D. R. Stuart, J.-P. Leclerc, M. Bertrand-Laperle, E. Villemure, H.-Y. Sun, S. Lasserre, N. Guimond, M. Lecavallier, K. Fagnou, J. Am. Chem. Soc. 2009, 131, 3291-3306
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 3291-3306
- Campeau, L.-C.¹ Stuart, D.R.² Leclerc, J.-P.³ Bertrand-Laperle, M.⁴ Villemure, E.⁵ Sun, H.-Y.⁶ Lasserre, S.⁷ Guimond, N.⁸ Lecavallier, M.⁹ Fagnou, K.¹⁰

19
- 64249118769
- e) B. Liégault, D. Lapointe, L. Caron, A. Vlassova, K. Fagnou, J. Org. Chem. 2009, 74, 1826-1834
- (2009) J. Org. Chem. , vol.74 , pp. 1826-1834
- Liégault, B.¹ Lapointe, D.² Caron, L.³ Vlassova, A.⁴ Fagnou, K.⁵

20
- 41449108490
- f) N. Lebrasseur, I. Larrosa, J. Am. Chem. Soc. 2008, 130, 2926-2927
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 2926-2927
- Lebrasseur, N.¹ Larrosa, I.²

21
- 35948944865
- g) M. Iwasaki, H. Yorimitsu, K. Oshima, Chem. Asian J. 2007, 2, 1430-1435
- (2007) Chem. Asian J. , vol.2 , pp. 1430-1435
- Iwasaki, M.¹ Yorimitsu, H.² Oshima, K.³

22
- 34547883488
- h) H. A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879-9884
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 9879-9884
- Chiong, H.A.¹ Pham, Q.-N.² Daugulis, O.³

23
- 34250864418
- i) S. Chuprakov, N. Chernyak, A. S. Dudnik, V. Gevorgyan, Org. Lett. 2007, 9, 2333-2336
- (2007) Org. Lett. , vol.9 , pp. 2333-2336
- Chuprakov, S.¹ Chernyak, N.² Dudnik, A.S.³ Gevorgyan, V.⁴

24
- 34249793676
- and references cited therein
- j) D. García-Cuadrado, P. de Mendoza, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2007, 129, 6880-6886, and references cited therein.
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 6880-6886
- García-Cuadrado, D.¹ De Mendoza, P.² Braga, A.A.C.³ Maseras, F.⁴ Echavarren, A.M.⁵

25
- 77951186891
- For selected recent examples of intramolecular C-H activation, see: a) Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, Angew. Chem. 2009, 121, 6213-6216
- (2009) Angew. Chem. , vol.121 , pp. 6213-6216
- Zhang, Y.-H.¹ Shi, B.-F.² Yu, J.-Q.³

26
- 70349777759
- Angew. Chem. Int. Ed. 2009, 48, 6097-6100
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6097-6100

27
- 67749102055
- b) C. Wang, I. Piel, F. Glorius, J. Am. Chem. Soc. 2009, 131, 4194-4195
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 4194-4195
- Wang, C.¹ Piel, I.² Glorius, F.³

28
- 57149107584
- c) S. J. Hwang, S. H. Cho, S. Chang, J. Am. Chem. Soc. 2008, 130, 16158-16159
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 16158-16159
- Hwang, S.J.¹ Cho, S.H.² Chang, S.³

29
- 70349694864
- d) V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2008, 120, 9604-9607
- (2008) Angew. Chem. , vol.120 , pp. 9604-9607
- Thirunavukkarasu, V.S.¹ Parthasarathy, K.² Cheng, C.-H.³

30
- 56749146314
- Angew. Chem. Int. Ed. 2008, 47, 9462-9465
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9462-9465

31
- 70249146933
- e) S. Kumar, H. Ila, H. Junjappa, J. Org. Chem. 2009, 74, 7046-7051
- (2009) J. Org. Chem. , vol.74 , pp. 7046-7051
- Kumar, S.¹ Ila, H.² Junjappa, H.³

32
- 70350580666
- f) S. Lage, U. Martínez-Estíbalez, N. Sotomayor, E. Lete, Adv. Synth. Catal. 2009, 351, 2460-2468
- (2009) Adv. Synth. Catal. , vol.351 , pp. 2460-2468
- Lage, S.¹ Martínez-Estíbalez, U.² Sotomayor, N.³ Lete, E.⁴

33
- 43849099804
- g) P. Franck, S. Hostyn, B. Dajka-Halász, Á. Polonka-Bálint, K. Monsieurs, P. Mátyus, B. U. W. Maes, Tetrahedron 2008, 64, 6030-6037.
- (2008) Tetrahedron , vol.64 , pp. 6030-6037
- Franck, P.¹ Hostyn, S.² Dajka-Halász, B.³ Polonka-Bálint, Á.⁴ Monsieurs, K.⁵ Mátyus, P.⁶ Maes, B.U.W.⁷

34
- 0003607021
- (Eds.: A. R. Katritzky C. W. Rees E. F. V. Scriven), Pergamon Oxford
- J. Elguero, Comprehensive Heterocyclic Chemistry, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, Vol.5.
- (1996) Comprehensive Heterocyclic Chemistry , vol.5
- Elguero, J.¹

35
- 13444266910
- T. D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, L. F. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. D. Anderson, E. G. Burton, J. N. Cogburn, S. A. Gregory, C. M. Koboldt, W. E. Perkins, K. Seibert, A.W. Veenhuizen, Y. Y. Zhang, P. C. Isakson, J. Med. Chem. 1997, 40, 1347-1365.
- (1997) J. Med. Chem. , vol.40 , pp. 1347-1365
- Penning, T.D.¹ Talley, J.J.² Bertenshaw, S.R.³ Carter, J.S.⁴ Collins, P.W.⁵ Docter, S.⁶ Graneto, M.J.⁷ Lee, L.F.⁸ Malecha, J.W.⁹ Miyashiro, J.M.¹⁰ Rogers, R.S.¹¹ Rogier, D.J.¹² Yu, S.S.¹³ Anderson, G.D.¹⁴ Burton, E.G.¹⁵ Cogburn, J.N.¹⁶ Gregory, S.A.¹⁷ Koboldt, C.M.¹⁸ Perkins, W.E.¹⁹ Seibert, K.²⁰ more..

36
- 0028129936
- M. Rinaldi-Carmona, F. Barth, M. Héaulme, D. Shire, B. Calandra, C. Congy, S. Martinez, J. Maruani, G. Néliat, D. Caput, P. Ferrara, P. Soubrié, J. C. Breliére, G. Le Fur, FEBS Lett. 1994, 350, 240-244.
- (1994) FEBS Lett. , vol.350 , pp. 240-244
- Rinaldi-Carmona, M.¹ Barth, F.² Héaulme, M.³ Shire, D.⁴ Calandra, B.⁵ Congy, C.⁶ Martinez, S.⁷ Maruani, J.⁸ Néliat, G.⁹ Caput, D.¹⁰ Ferrara, P.¹¹ Soubrié, P.¹² Breliére, J.C.¹³ Le Fur, G.¹⁴

37
- 0030572496
- N. K. Terrett, A. S. Bell, D. Brown, P. Ellis, Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824.
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1819-1824
- Terrett, N.K.¹ Bell, A.S.² Brown, D.³ Ellis, P.⁴

38
- 35148816953
- G. P. Lahm, T. M. Stevenson, T. P. Selby, J. H. Freudenberger, D. Cordova, L. Flexner, C. A. Bellin, C. M. Dubas, B. K. Smith, K. A. Hughes, J. G. Hollingshaus, C. E. Clark, E. A. Benner, Bioorg. Med. Chem. Lett. 2007, 17, 6274-6279.
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 6274-6279
- Lahm, G.P.¹ Stevenson, T.M.² Selby, T.P.³ Freudenberger, J.H.⁴ Cordova, D.⁵ Flexner, L.⁶ Bellin, C.A.⁷ Dubas, C.M.⁸ Smith, B.K.⁹ Hughes, K.A.¹⁰ Hollingshaus, J.G.¹¹ Clark, C.E.¹² Benner, E.A.¹³

39
- 67749101415
- R. Goikhman, T. L. Jacques, D. Sames, J. Am. Chem. Soc. 2009, 131, 3042-3048.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 3042-3048
- Goikhman, R.¹ Jacques, T.L.² Sames, D.³

40
- 33744733072
- a) C. Blaszykowski, E. Aktoudianakis, C. Bressy, D. Alberico, M. Lautens, Org. Lett. 2006, 8, 2043-2045
- (2006) Org. Lett. , vol.8 , pp. 2043-2045
- Blaszykowski, C.¹ Aktoudianakis, E.² Bressy, C.³ Alberico, D.⁴ Lautens, M.⁵

41
- 41149168872
- b) C. Blaszykowski, E. Aktoudianakis, D. Alberico, C. Bressy, D. G. Hulcoop, F. Jafarpour, A. Joushaghani, B. Laleu, M. Lautens, J. Org. Chem. 2008, 73, 1888-1897
- (2008) J. Org. Chem. , vol.73 , pp. 1888-1897
- Blaszykowski, C.¹ Aktoudianakis, E.² Alberico, D.³ Bressy, C.⁴ Hulcoop, D.G.⁵ Jafarpour, F.⁶ Joushaghani, A.⁷ Laleu, B.⁸ Lautens, M.⁹

42
- 56449086514
- c) B. Laleu, M. Lautens, J. Org. Chem. 2008, 73, 9164-9167.
- (2008) J. Org. Chem. , vol.73 , pp. 9164-9167
- Laleu, B.¹ Lautens, M.²

43
- 33751354638
- N. Arai, M. Takahashi, M. Mitani, A. Mori, Synlett 2006, 3170-3172.
- (2006) Synlett , pp. 3170-3172
- Arai, N.¹ Takahashi, M.² Mitani, M.³ Mori, A.⁴

44
- 0034656740
- a) D. B. Grotjahn, D. Combs, S. Van, G. Aguirre, F. Ortega, Inorg. Chem. 2000, 39, 2080-2086
- (2000) Inorg. Chem. , vol.39 , pp. 2080-2086
- Grotjahn, D.B.¹ Combs, D.² Van, S.³ Aguirre, G.⁴ Ortega, F.⁵

45
- 75349095055
- b) S. Hernández, I. Moreno, R. SanMartin, G. Gómez, M. T. Herrero, E. Domínguez, J. Org. Chem. 2010, 75, 434-441.
- (2010) J. Org. Chem. , vol.75 , pp. 434-441
- Hernández, S.¹ Moreno, I.² Sanmartin, R.³ Gómez, G.⁴ Herrero, M.T.⁵ Domínguez, E.⁶

46
- 0010372638
- R. Grigg, V. Sridharan, P. Stevenson, S. Sukirthalingam, T. Worakun, Tetrahedron 1990, 46, 4003-4018.
- (1990) Tetrahedron , vol.46 , pp. 4003-4018
- Grigg, R.¹ Sridharan, V.² Stevenson, P.³ Sukirthalingam, S.⁴ Worakun, T.⁵

47
- 53849088886
- For Pd-catalyzed intramolecular C-H activation of 1,2,3-triazoles, see: a) L. Ackermann, R. Vicente, R. Born, Adv. Synth. Catal. 2008, 350, 741-748
- (2008) Adv. Synth. Catal. , vol.350 , pp. 741-748
- Ackermann, L.¹ Vicente, R.² Born, R.³

48
- 33745378035
- b) W.-L. Chen, C.-L. Su, X. Huang, Synlett 2006, 1446-1448.
- (2006) Synlett , pp. 1446-1448
- Chen, W.-L.¹ Su, C.-L.² Huang, X.³

49
- 52449117145
- a) Y. H. Kim, H. Lee, Y. J. Kim, B. T. Kim, J.-N. Heo, J. Org. Chem. 2008, 73, 495-501
- (2008) J. Org. Chem. , vol.73 , pp. 495-501
- Kim, Y.H.¹ Lee, H.² Kim, Y.J.³ Kim, B.T.⁴ Heo, J.-N.⁵

50
- 54049114342
- b) J. K. Kim, Y. H. Kim, H. T. Nam, B. T. Kim, J.-N. Heo, Org. Lett. 2008, 10, 3543-3546
- (2008) Org. Lett. , vol.10 , pp. 3543-3546
- Kim, J.K.¹ Kim, Y.H.² Nam, H.T.³ Kim, B.T.⁴ Heo, J.-N.⁵

51
- 65949115295
- c) Y. L. Choi, C.-M. Yu, B. T. Kim, J.-N. Heo, J. Org. Chem. 2009, 74, 3948-3951
- (2009) J. Org. Chem. , vol.74 , pp. 3948-3951
- Choi, Y.L.¹ Yu, C.-M.² Kim, B.T.³ Heo, J.-N.⁴

52
- 76949095786
- d) Y.-H. Goh, G. Kim, B. T. Kim, J.-N. Heo, Heterocycles 2010, 80, 669-677.
- (2010) Heterocycles , vol.80 , pp. 669-677
- Goh, Y.-H.¹ Kim, G.² Kim, B.T.³ Heo, J.-N.⁴

53
- 0003402765
- VCH, Weinheim
- For reviews on salt effects, see: a) A. Loupy, B. Tchoubar, Salt Effects in Organic and Organometallic Chemistry, VCH, Weinheim, 1992
- (1992) Salt Effects in Organic and Organometallic Chemistry
- Loupy, A.¹ Tchoubar, B.²

54
- 0037016413
- b) K. Fagnou, M. Lautens, Angew. Chem. 2002, 114, 26-49
- (2002) Angew. Chem. , vol.114 , pp. 26-49
- Fagnou, K.¹ Lautens, M.²

55
- 33745876993
- Angew. Chem. Int. Ed. 2002, 41, 26-47.
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 26-47

56
- 57549099215
- and references cited therein
- R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461-1473, and references cited therein.
- (2008) Acc. Chem. Res. , vol.41 , pp. 1461-1473
- Martin, R.¹ Buchwald, S.L.²

57
- 3042819291
- a) F. Rataboul, A. Zapf, R. Jackstell, S. Harkal, T. Riermeier, A. Monsees, U. Dingerdissen, M. Beller, Chem. Eur. J. 2004, 10, 2983-2990
- (2004) Chem. Eur. J. , vol.10 , pp. 2983-2990
- Rataboul, F.¹ Zapf, A.² Jackstell, R.³ Harkal, S.⁴ Riermeier, T.⁵ Monsees, A.⁶ Dingerdissen, U.⁷ Beller, M.⁸

58
- 1642580702
- b) A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dingerdissen, M. Beller, Chem. Commun. 2004, 38-39.
- (2004) Chem. Commun. , pp. 38-39
- Zapf, A.¹ Jackstell, R.² Rataboul, F.³ Riermeier, T.⁴ Monsees, A.⁵ Fuhrmann, C.⁶ Shaikh, N.⁷ Dingerdissen, U.⁸ Beller, M.⁹

59
- 74949132564
- S. A. Ohnmacht, A. J. Culshaw, M. F. Greaney, Org. Lett. 2010, 12, 224-226.
- (2010) Org. Lett. , vol.12 , pp. 224-226
- Ohnmacht, S.A.¹ Culshaw, A.J.² Greaney, M.F.³

60
- 77956362828
- or on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax.: (internat.) + 44 1223/336-033; e-mail: deposit @ccdc.cam.ac.uk]
- Crystallographic data (excluding structure factors) for the structure 3e reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no.CCDC 771302. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif or on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax.: (internat.) + 44 1223/336-033; e-mail: deposit @ccdc.cam.ac.uk]

61
- 77956378469
- [2e]. (Image prsented)
- [2e]. (Image prsented).

62
- 43849097670
- We are grateful to a referee for pointing out that the pyrazole group could serve as a directing group, affording the arylated product on the anisole ring of compound 3e. In our case of palladium-catalyzed conditions we could observe no or little anisole-substituted product. For ruthenium-catalyzed direct arylation of N-arylpyrazoles as a directing group, see: a) L. Ackermann, A. Althammer, R. Born, Tetrahedron 2008, 64, 6115-6124
- (2008) Tetrahedron , vol.64 , pp. 6115-6124
- Ackermann, L.¹ Althammer, A.² Born, R.³

63
- 36549071920
- b) L. Ackermann, A. Althammer, R. Born, Synlett 2007, 2833-2836.
- (2007) Synlett , pp. 2833-2836
- Ackermann, L.¹ Althammer, A.² Born, R.³

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