SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 52, Issue 49, 2013, Pages 13086-13090

Metal-free aryltrifluoromethylation of activated alkenes

(5) Kong, Wangqing a Casimiro, Maria a Fuentes, Noelia a Merino, Estíbaliz a Nevado, Cristina a

a UNIVERSITY OF ZURICH (Switzerland)

Author keywords

alkenes; arenes; iodine; Togni reagent; trifluoromethylation

Indexed keywords

ACTIVATED ALKENES; ARENES; OXINDOLES; TOGNI REAGENT; TRIFLUOROMETHYLATION;

CHEMICAL REACTIONS; CHEMISTRY; IODINE; OLEFINS;

HYDROCARBONS;

EID: 84888618922 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201307377 Document Type: Article

Times cited : (280)

References (72)

1
- 84891565619
- in, Wiley-VCH, Weinheim
- P. Kirsch, in Modern Fluoroorganic Chemistry: Synthesis Reactivity Applications, Wiley-VCH, Weinheim, 2004
- (2004) Modern Fluoroorganic Chemistry: Synthesis Reactivity Applications
- Kirsch, P.¹

2
- 79751479551
- in, Wiley-Blackwell, Chichester
- I. Ojima, in Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, 2009
- (2009) Fluorine in Medicinal Chemistry and Chemical Biology
- Ojima, I.¹

3
- 38149070200
- S. Purser, P. R. Moore, S. Swallow, V. Governeur, Chem. Soc. Rev. 2008, 37, 320-330.
- (2008) Chem. Soc. Rev. , vol.37 , pp. 320-330
- Purser, S.¹ Moore, P.R.² Swallow, S.³ Governeur, V.⁴

4
- 79957603696
- T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470-477
- (2011) Nature , vol.473 , pp. 470-477
- Furuya, T.¹ Kamlet, A.S.² Ritter, T.³

5
- 79958141712
- O. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475-4521
- (2011) Chem. Rev. , vol.111 , pp. 4475-4521
- Tomashenko, O.¹ Grushin, V.V.²

6
- 84863844406
- X. F. Wu, H. Neumann, M. Beller, Chem. Asian J. 2012, 7, 1744-1754
- (2012) Chem. Asian J. , vol.7 , pp. 1744-1754
- Wu, X.F.¹ Neumann, H.² Beller, M.³

7
- 84864691575
- Y. Ye, M. S. Sanford, Synlett 2012, 2005-2013
- (2012) Synlett , pp. 2005-2013
- Ye, Y.¹ Sanford, M.S.²

8
- 54549103372
- T. Furuya, C. A. Kuttruff, T. Ritter, Curr. Opin. Drug Discovery Dev. 2008, 11, 803-819
- (2008) Curr. Opin. Drug Discovery Dev. , vol.11 , pp. 803-819
- Furuya, T.¹ Kuttruff, C.A.² Ritter, T.³

9
- 78349266515
- S. Lectard, Y. Hamashima, M. Sodeoka, Adv. Synth. Catal. 2010, 352, 2708-2732.
- (2010) Adv. Synth. Catal. , vol.352 , pp. 2708-2732
- Lectard, S.¹ Hamashima, Y.² Sodeoka, M.³

10
- 67549150783
- M. Oishi, H. Kondo, H. Amii, Chem. Commun. 2009, 1909-1911
- (2009) Chem. Commun. , pp. 1909-1911
- Oishi, M.¹ Kondo, H.² Amii, H.³

11
- 79960643289
- H. Morimoto, T. Tsubogo, N. D. Litvinas, J. F. Hartwig, Angew. Chem. 2011, 123, 3877-3882
- (2011) Angew. Chem. , vol.123 , pp. 3877-3882
- Morimoto, H.¹ Tsubogo, T.² Litvinas, N.D.³ Hartwig, J.F.⁴

12
- 79953675070
- Angew. Chem. Int. Ed. 2011, 50, 3793-3798
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 3793-3798

13
- 77954055124
- E. J. Cho, T. D. Senecal, T. Y. Zhang, D. A. Watson, S. L. Buchwald, Science 2010, 328, 1679-1681
- (2010) Science , vol.328 , pp. 1679-1681
- Cho, E.J.¹ Senecal, T.D.² Zhang, T.Y.³ Watson, D.A.⁴ Buchwald, S.L.⁵

14
- 84864237977
- X.-G. Zhang, H.-X. Dai, M. Wasa, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 11948-11951
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 11948-11951
- Zhang, X.-G.¹ Dai, H.-X.² Wasa, M.³ Yu, J.-Q.⁴

15
- 77952859294
- L. Chu, F.-L. Qing, J. Am. Chem. Soc. 2010, 132, 7262-7263
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 7262-7263
- Chu, L.¹ Qing, F.-L.²

16
- 84858220651
- A. T. Parsons, S. L. Buchwald, Angew. Chem. 2011, 123, 9286-9289
- (2011) Angew. Chem. , vol.123 , pp. 9286-9289
- Parsons, A.T.¹ Buchwald, S.L.²

17
- 80052851561
- Angew. Chem. Int. Ed. 2011, 50, 9120-9123
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 9120-9123

18
- 80054752885
- X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 16410-16413
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 16410-16413
- Wang, X.¹ Ye, Y.² Zhang, S.³ Feng, J.⁴ Xu, Y.⁵ Zhang, Y.⁶ Wang, J.⁷

19
- 80053306621
- J. Xu, Y. Fu, D.-F. Luo, Y.-Y. Jiang, B. Xiao, Z.-J. Liu, T.-J. Gong, L. Liu, J. Am. Chem. Soc. 2011, 133, 15300-15303
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 15300-15303
- Xu, J.¹ Fu, Y.² Luo, D.-F.³ Jiang, Y.-Y.⁴ Xiao, B.⁵ Liu, Z.-J.⁶ Gong, T.-J.⁷ Liu, L.⁸

20
- 84863427463
- R. Shimizu, H. Egami, Y. Hamashima, M. Sodeoka, Angew. Chem. 2012, 124, 4655-4658
- (2012) Angew. Chem. , vol.124 , pp. 4655-4658
- Shimizu, R.¹ Egami, H.² Hamashima, Y.³ Sodeoka, M.⁴

21
- 84860760651
- Angew. Chem. Int. Ed. 2012, 51, 4577-4580
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4577-4580

22
- 84863464636
- S. Mizuta, O. Galicia-Lõpez, K. M. Engle, S. Verhoog, K. Wheelhouse, G. Rassias, V. Gouverneur, Chem. Eur. J. 2012, 18, 8583-8587
- (2012) Chem. Eur. J. , vol.18 , pp. 8583-8587
- Mizuta, S.¹ Galicia-Lõpez, O.² Engle, K.M.³ Verhoog, S.⁴ Wheelhouse, K.⁵ Rassias, G.⁶ Gouverneur, V.⁷

23
- 84885680270
- Z. He, M. Hu, T. Luo, L. Li, J. Hu, Angew. Chem. 2012, 124, 11713-11715
- (2012) Angew. Chem. , vol.124 , pp. 11713-11715
- He, Z.¹ Hu, M.² Luo, T.³ Li, L.⁴ Hu, J.⁵

24
- 84868549571
- Angew. Chem. Int. Ed. 2012, 51, 11545-11547
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 11545-11547

25
- 84867784149
- A. Studer, Angew. Chem. 2012, 124, 9082-9090
- (2012) Angew. Chem. , vol.124 , pp. 9082-9090
- Studer, A.¹

26
- 84865853817
- Angew. Chem. Int. Ed. 2012, 51, 8950-8958
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8950-8958

27
- 84874056108
- S. Mizuta, S. Verhoog, K. M. Engle, T. Khotavivattana, M. O'Duill, K. Wheelhouse, G. Rassias, M. Médebielle, V. Gouverneur, J. Am. Chem. Soc. 2013, 135, 2505-2508
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 2505-2508
- Mizuta, S.¹ Verhoog, S.² Engle, K.M.³ Khotavivattana, T.⁴ O'Duill, M.⁵ Wheelhouse, K.⁶ Rassias, G.⁷ Médebielle, M.⁸ Gouverneur, V.⁹

28
- 84885660804
- H. Egami, S. Kawamura, A. Miyazaki, M. Sodeoka, Angew. Chem. 2013, 125, 7995-7998
- (2013) Angew. Chem. , vol.125 , pp. 7995-7998
- Egami, H.¹ Kawamura, S.² Miyazaki, A.³ Sodeoka, M.⁴

29
- 84880375460
- Angew. Chem. Int. Ed. 2013, 52, 7841-7844.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 7841-7844

30
- 84864443774
- R. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2012, 134, 12462-12465
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 12462-12465
- Zhu, R.¹ Buchwald, S.L.²

31
- 84861835292
- P. G. Janson, I. Ghoneim, N. O. Ilchenko, K. J. Szabõ, Org. Lett. 2012, 14, 2882-2885
- (2012) Org. Lett. , vol.14 , pp. 2882-2885
- Janson, P.G.¹ Ghoneim, I.² Ilchenko, N.O.³ Szabõ, K.J.⁴

32
- 84868095946
- C. Feng, T.-P. Loh, Chem. Sci. 2012, 3, 3458-3462
- (2012) Chem. Sci. , vol.3 , pp. 3458-3462
- Feng, C.¹ Loh, T.-P.²

33
- 79958014772
- C.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, J.-C. Xiao, Chem. Commun. 2011, 47, 6632-6634.
- (2011) Chem. Commun. , vol.47 , pp. 6632-6634
- Zhang, C.-P.¹ Wang, Z.-L.² Chen, Q.-Y.³ Zhang, C.-T.⁴ Gu, Y.-C.⁵ Xiao, J.-C.⁶

34
- 84862908150
- X. Mu, H.-Y. Wang, Y.-I. Guo, G. Liu, J. Am. Chem. Soc. 2012, 134, 878-881.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 878-881
- Mu, X.¹ Wang, H.-Y.² Guo, Y.-I.³ Liu, G.⁴

35
- 84879381137
- H. Egami, R. Shimizu, S. Kawamura, M. Sodeoka, Angew. Chem. 2013, 125, 4092-4095
- (2013) Angew. Chem. , vol.125 , pp. 4092-4095
- Egami, H.¹ Shimizu, R.² Kawamura, S.³ Sodeoka, M.⁴

36
- 84875718798
- Angew. Chem. Int. Ed. 2013, 52, 4000-4003
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 4000-4003

37
- 84883546398
- H. Egami, R. Shimizu, M. Sodeoka, J. Fluorine Chem. 2013, 152, 51-55.
- (2013) J. Fluorine Chem. , vol.152 , pp. 51-55
- Egami, H.¹ Shimizu, R.² Sodeoka, M.³

38
- 84873897155
- Y. Li, A. Studer, Angew. Chem. 2012, 124, 8345-8348
- (2012) Angew. Chem. , vol.124 , pp. 8345-8348
- Li, Y.¹ Studer, A.²

39
- 84864871408
- Angew. Chem. Int. Ed. 2012, 51, 8221-8224.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8221-8224

40
- 33644919105
- For pioneering reports on the activation of 1 with Lewis acids, see P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579-2586
- (2006) Chem. Eur. J. , vol.12 , pp. 2579-2586
- Eisenberger, P.¹ Gischig, S.² Togni, A.³

41
- 74549217091
- R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, A. Togni, Angew. Chem. 2009, 121, 4396-4400
- (2009) Angew. Chem. , vol.121 , pp. 4396-4400
- Koller, R.¹ Stanek, K.² Stolz, D.³ Aardoom, R.⁴ Niedermann, K.⁵ Togni, A.⁶

42
- 70349961605
- Angew. Chem. Int. Ed. 2009, 48, 4332-4336
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 4332-4336

43
- 53249153081
- I. Kieltsch, P. Eisenberger, A. Togni, Angew. Chem. 2007, 119, 768-771
- (2007) Angew. Chem. , vol.119 , pp. 768-771
- Kieltsch, I.¹ Eisenberger, P.² Togni, A.³

44
- 33846525992
- Angew. Chem. Int. Ed. 2007, 46, 754-757
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 754-757

45
- 77950854848
- A. E. Allen, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 4986-4987.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 4986-4987
- Allen, A.E.¹ MacMillan, D.W.C.²

46
- 79952601820
- Y. Kang, L. H. Gade, J. Am. Chem. Soc. 2011, 133, 3658-3667
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 3658-3667
- Kang, Y.¹ Gade, L.H.²

47
- 67849129077
- Y. Kita, K. Morimoto, M. Ito, C. Ogawa, A. Goto, T. Dohi, J. Am. Chem. Soc. 2009, 131, 1668-1669
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 1668-1669
- Kita, Y.¹ Morimoto, K.² Ito, M.³ Ogawa, C.⁴ Goto, A.⁵ Dohi, T.⁶

48
- 70749096223
- R. Fan, Y. Ye, Org. Lett. 2009, 11, 5174-5177
- (2009) Org. Lett. , vol.11 , pp. 5174-5177
- Fan, R.¹ Ye, Y.²

49
- 0011723162
- H. Tohma, S. Takzawa, T. Maegawa, Y. Kita, Angew. Chem. 2000, 112, 1362-1364
- (2000) Angew. Chem. , vol.112 , pp. 1362-1364
- Tohma, H.¹ Takzawa, S.² Maegawa, T.³ Kita, Y.⁴

50
- 0034599884
- Angew. Chem. Int. Ed. 2000, 39, 1306-1308
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1306-1308

51
- 84879881788
- C. Xu, J. Liu, W. Ming, Y. Liu, J. Liu, M. Wang, Q. Liu, Chem. Eur. J. 2013, 19, 9104-9109.
- (2013) Chem. Eur. J. , vol.19 , pp. 9104-9109
- Xu, C.¹ Liu, J.² Ming, W.³ Liu, Y.⁴ Liu, J.⁵ Wang, M.⁶ Liu, Q.⁷

52
- 80052080149
- T. de Haro, C. Nevado, Angew. Chem. 2011, 123, 936-940
- (2011) Angew. Chem. , vol.123 , pp. 936-940
- De Haro, T.¹ Nevado, C.²

53
- 78751516435
- Angew. Chem. Int. Ed. 2011, 50, 906-910.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 906-910

54
- 84879330013
- W. Kong, P. Feige, T. de Haro, C. Nevado, Angew. Chem. 2013, 125, 2529-2533
- (2013) Angew. Chem. , vol.125 , pp. 2529-2533
- Kong, W.¹ Feige, P.² De Haro, T.³ Nevado, C.⁴

55
- 84874233580
- Angew. Chem. Int. Ed. 2013, 52, 2469-2473
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 2469-2473

56
- 84885144334
- W. Kong, M. Casimiro, E. Merino, C. Nevado, J. Am. Chem. Soc. 2013, 135, 14480-14483.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 14480-14483
- Kong, W.¹ Casimiro, M.² Merino, E.³ Nevado, C.⁴

57
- 84888603931
- CCDC 940668 (3 d) and CCDC 945177 (3 l) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.

58
- 84877728653
- M.-B. Zhou, R.-J. Song, X.-H. Ouyang, Y. Liu, W.-T. Wei, G.-B. Deng, J.-H. Li, Chem. Sci. 2013, 4, 2690-2694
- (2013) Chem. Sci. , vol.4 , pp. 2690-2694
- Zhou, M.-B.¹ Song, R.-J.² Ouyang, X.-H.³ Liu, Y.⁴ Wei, W.-T.⁵ Deng, G.-B.⁶ Li, J.-H.⁷

59
- 31544455027
- L. C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 581-590
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 581-590
- Campeau, L.C.¹ Parisien, M.² Jean, A.³ Fagnou, K.⁴

60
- 25444475266
- D. Kalyani, M. Sanford, Org. Lett. 2005, 7, 4149-4152.
- (2005) Org. Lett. , vol.7 , pp. 4149-4152
- Kalyani, D.¹ Sanford, M.²

61
- 53749087530
- U. K. Wefelscheid, M. Berndt, H. U. Reissig, Eur. J. Org. Chem. 2008, 3635-3646
- (2008) Eur. J. Org. Chem. , pp. 3635-3646
- Wefelscheid, U.K.¹ Berndt, M.² Reissig, H.U.³

62
- 70349779340
- T. Tsubusaki, H. Nishino, Tetrahedron 2009, 65, 9448-9459.
- (2009) Tetrahedron , vol.65 , pp. 9448-9459
- Tsubusaki, T.¹ Nishino, H.²

63
- 0037870758
- E. Miyazawa, T. Sakamoto, Y. Kikugawa, J. Org. Chem. 2003, 68, 5429-5432
- (2003) J. Org. Chem. , vol.68 , pp. 5429-5432
- Miyazawa, E.¹ Sakamoto, T.² Kikugawa, Y.³

64
- 0011234079
- C. H. Chen, K. E. Brighty, F. M. Michaels, J. Org. Chem. 1981, 46, 361-367
- (1981) J. Org. Chem. , vol.46 , pp. 361-367
- Chen, C.H.¹ Brighty, K.E.² Michaels, F.M.³

65
- 0035974414
- J. J. Sepiol, J. Wilamowski, Tetrahedron Lett. 2001, 42, 5287-5289.
- (2001) Tetrahedron Lett. , vol.42 , pp. 5287-5289
- Sepiol, J.J.¹ Wilamowski, J.²

66
- 77957856689
- S. Jaegli, J. Dufour, H. Wei, T. Piou, X. Duan, J.-P. Vors, L. Neuville, J. Zhu, Org. Lett. 2010, 12, 4498-4501
- (2010) Org. Lett. , vol.12 , pp. 4498-4501
- Jaegli, S.¹ Dufour, J.² Wei, H.³ Piou, T.⁴ Duan, X.⁵ Vors, J.-P.⁶ Neuville, L.⁷ Zhu, J.⁸

67
- 84941944744
- H. Wei, T. Piou, J. Dufour, L. Neuville, J. Zhu, Org. Lett. 2011, 13, 2244-2247
- (2011) Org. Lett. , vol.13 , pp. 2244-2247
- Wei, H.¹ Piou, T.² Dufour, J.³ Neuville, L.⁴ Zhu, J.⁵

68
- 84881117628
- Y. Meng, L.-N. Guo, H. Wang, X.-H. Duan, Chem. Commun. 2013, 49, 7540-7542.
- (2013) Chem. Commun. , vol.49 , pp. 7540-7542
- Meng, Y.¹ Guo, L.-N.² Wang, H.³ Duan, X.-H.⁴

69
- 77957712903
- T. Wang, H.-F. Wang, X.-P. Yan, CrystEngComm 2010, 12, 3177-3182.
- (2010) CrystEngComm , vol.12 , pp. 3177-3182
- Wang, T.¹ Wang, H.-F.² Yan, X.-P.³

70
- 0039721948
- see Ref. [8a] and:, C. W. Perkins, J. C. Martin, A. J. Arduengo, W. Lau, A. Alegria, J. K. Kochi, J. Am. Chem. Soc. 1980, 102, 7753-7759.
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7753-7759
- Perkins, C.W.¹ Martin, J.C.² Arduengo, A.J.³ Lau, W.⁴ Alegria, A.⁵ Kochi, J.K.⁶

71
- 84888584681
- B. Zhang, C. Mück-Lichtenfeld, C. G. Daniliuc, A. Studer, Angew. Chem. 2013, 125, 10992-10995
- (2013) Angew. Chem. , vol.125 , pp. 10992-10995
- Zhang, B.¹ Mück-Lichtenfeld, C.² Daniliuc, C.G.³ Studer, A.⁴

72
- 84885099555
- 10792- 10795.
- Angew. Chem. Int. Ed. 2013, 52, 10792- 10795.
- (2013) Angew. Chem. Int. Ed. , pp. 52

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.