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Angewandte Chemie - International Edition

Volumn 52, Issue 41, 2013, Pages 10792-10795

6-Trifluoromethyl-phenanthridines through radical trifluoromethylation of isonitriles

(4) Zhang, Bo a Mück Lichtenfeld, Christian a Daniliuc, Constantin Gabriel a Studer, Armido a

a UNIVERSITY OF MÜNSTER (Germany)

Author keywords

arenes; aromatic substitution; iodine(III) reagents; radical reactions; trifluoromethylation

Indexed keywords

REACTION KINETICS; REAGENTS; TRANSITION METALS;

ARENES; AROMATIC SUBSTITUTIONS; ISONITRILES; RADICAL INITIATORS; RADICAL PRECURSOR; RADICAL REACTIONS; TRIFLUOROMETHYLATION;

AROMATIC HYDROCARBONS;

FLUORINATED HYDROCARBON; IODINE; NITRILE; PHENANTHRIDINE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; METHYLATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HALOGENATION; HYDROCARBONS, FLUORINATED; IODINE; METHYLATION; MODELS, MOLECULAR; NITRILES; PHENANTHRIDINES;

EID: 84885099555 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201306082 Document Type: Article

Times cited : (324)

References (66)

1
- 34848848499
- K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886
- (2007) Science , vol.317 , pp. 1881-1886
- Müller, K.¹ Faeh, C.² Diederich, F.³

2
- 38149070200
- S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, 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 Gouverneur, V.⁴

3
- 79958141712
- O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475-4521
- (2011) Chem. Rev. , vol.111 , pp. 4475-4521
- Tomashenko, O.A.¹ Grushin, V.V.²

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
- 79952189007
- S. Roy, B. T. Gregg, G. W. Gribble, V.-D. Le, S. Roy, Tetrahedron 2011, 67, 2161-2195
- (2011) Tetrahedron , vol.67 , pp. 2161-2195
- Roy, S.¹ Gregg, B.T.² Gribble, G.W.³ Le, V.-D.⁴ Roy, S.⁵

6
- 84869454952
- T. Liu, Q. Shen, Eur. J. Org. Chem. 2012, 6679-6687
- (2012) Eur. J. Org. Chem. , pp. 6679-6687
- Liu, T.¹ Shen, Q.²

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

8
- 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

9
- 84867784149
- Review:, A. Studer, Angew. Chem. 2012, 124, 9082-9090
- (2012) Angew. Chem. , vol.124 , pp. 9082-9090
- Studer, A.¹

10
- 84865853817
- Angew. Chem. Int. Ed. 2012, 51, 8950-8958.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8950-8958

11
- 83055177179
- D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224-228
- (2011) Nature , vol.480 , pp. 224-228
- Nagib, D.A.¹ Macmillan, D.W.C.²

12
- 80052298009
- Y. Ji, T. Brueckl, R. D. Baxter, Y. Fujiwara, I. B. Seiple, S. Su, D. G. Blackmond, P. S. Baran, Proc. Natl. Acad. Sci. USA 2011, 108, 14411-14415
- (2011) Proc. Natl. Acad. Sci. USA , vol.108 , pp. 14411-14415
- Ji, Y.¹ Brueckl, T.² Baxter, R.D.³ Fujiwara, Y.⁴ Seiple, I.B.⁵ Su, S.⁶ Blackmond, D.G.⁷ Baran, P.S.⁸

13
- 80054701792
- Y. Ye, S. H. Lee, M. S. Sanford, Org. Lett. 2011, 13, 5464-5467
- (2011) Org. Lett. , vol.13 , pp. 5464-5467
- Ye, Y.¹ Lee, S.H.² Sanford, M.S.³

14
- 84862777465
- N. Iqbal, S. Choi, E. Ko, E. J. Cho, Tetrahedron Lett. 2012, 53, 2005-2008
- (2012) Tetrahedron Lett. , vol.53 , pp. 2005-2008
- Iqbal, N.¹ Choi, S.² Ko, E.³ Cho, E.J.⁴

15
- 84870541226
- Y. Fujiwara, J. A. Dixon, F. O'Hara, E. D. Funder, D. D. Dixon, R. A. Rodriguez, R. D. Baxter, B. Herlé, N. Sach, M. R. Collins, Y. Ishihara, P. S. Baran, Nature 2012, 492, 95-99
- (2012) Nature , vol.492 , pp. 95-99
- Fujiwara, Y.¹ Dixon, J.A.² O'Hara, F.³ Funder, E.D.⁴ Dixon, D.D.⁵ Rodriguez, R.A.⁶ Baxter, R.D.⁷ Herlé, B.⁸ Sach, N.⁹ Collins, M.R.¹⁰ Ishihara, Y.¹¹ Baran, P.S.¹²

16
- 84867340538
- Y. Ye, S. A. Künzi, M. S. Sanford, Org. Lett. 2012, 14, 4979-4981.
- (2012) Org. Lett. , vol.14 , pp. 4979-4981
- Ye, Y.¹ Künzi, S.A.² Sanford, M.S.³

17
- 84874639959
- For the formation of trifluoromethylarenes through trifluoromethylation of arynes, see:, Y. Zeng, L. Zhang, Y. Zhao, C. Ni, J. Zhao, J. Hu, J. Am. Chem. Soc. 2013, 135, 2955-2958.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 2955-2958
- Zeng, Y.¹ Zhang, L.² Zhao, Y.³ Ni, C.⁴ Zhao, J.⁵ Hu, J.⁶

18
- 0007660828
- D. P. Curran, H. Liu, J. Am. Chem. Soc. 1992, 114, 5863-5864
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 5863-5864
- Curran, D.P.¹ Liu, H.²

19
- 0040637800
- D. P. Curran, S.-B. Ko, H. Josien, Angew. Chem. 1995, 107, 2948
- (1995) Angew. Chem. , vol.107 , pp. 2948
- Curran, D.P.¹ Ko, S.-B.² Josien, H.³

20
- 0000096744
- Angew. Chem. Int. Ed. Engl. 1995, 34, 2683-2684
- (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2683-2684

21
- 0029083476
- D. Nanni, P. Pareschi, C. Rizzoli, P. Sgarabotto, T. Tundo, Tetrahedron 1995, 51, 9045-9062
- (1995) Tetrahedron , vol.51 , pp. 9045-9062
- Nanni, D.¹ Pareschi, P.² Rizzoli, C.³ Sgarabotto, P.⁴ Tundo, T.⁵

22
- 0034829343
- S. Yamago, H. Miyazoe, R. Goto, M. Hashidume, T. Sawazaki, J.-i. Yoshida, J. Am. Chem. Soc. 2001, 123, 3697-3705; reviews
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 3697-3705
- Yamago, S.¹ Miyazoe, H.² Goto, R.³ Hashidume, M.⁴ Sawazaki, T.⁵ Yoshida, J.-I.⁶

23
- 0001451085
- I. Ryu, N. Sonoda, D. P. Curran, Chem. Rev. 1996, 96, 177-194
- (1996) Chem. Rev. , vol.96 , pp. 177-194
- Ryu, I.¹ Sonoda, N.² Curran, D.P.³

24
- 84879164199
- in (Eds.: C. Chatgilialoglu, A. Studer), Wiley, Chichester
- D. Spagnolo, D. Nanni, in Encyclopedia of Radicals in Chemistry, Biology and Materials, Vol. 2 (Eds.:, C. Chatgilialoglu, A. Studer,), Wiley, Chichester, 2012, pp. 1019-1057.
- (2012) Encyclopedia of Radicals in Chemistry, Biology and Materials, Vol. 2 , pp. 1019-1057
- Spagnolo, D.¹ Nanni, D.²

25
- 0024453167
- S. Simeon, J. L. Rios, A. Villar, Pharmazie 1989, 44, 593-597
- (1989) Pharmazie , vol.44 , pp. 593-597
- Simeon, S.¹ Rios, J.L.² Villar, A.³

26
- 0019425250
- S. D. Phillips, R. N. Castle, J. Heterocycl. Chem. 1981, 18, 223-232
- (1981) J. Heterocycl. Chem. , vol.18 , pp. 223-232
- Phillips, S.D.¹ Castle, R.N.²

27
- 3242758865
- O. B. Abdel-Halim, T. Morikawa, S. Ando, H. Matsuda, M. Yoshikawa, J. Nat. Prod. 2004, 67, 1119-1124
- (2004) J. Nat. Prod. , vol.67 , pp. 1119-1124
- Abdel-Halim, O.B.¹ Morikawa, T.² Ando, S.³ Matsuda, H.⁴ Yoshikawa, M.⁵

28
- 37849025587
- L. Sripada, J. A. Teske, A. Deiters, Org. Biomol. Chem. 2008, 6, 263-265.
- (2008) Org. Biomol. Chem. , vol.6 , pp. 263-265
- Sripada, L.¹ Teske, J.A.² Deiters, A.³

29
- 33644919105
- O. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579-2586
- (2006) Chem. Eur. J. , vol.12 , pp. 2579-2586
- Eisenberger, O.¹ Gischig, S.² Togni, A.³

30
- 77955577649
- M. S. Wiehn, E. V. Vinogradova, A. Togni, J. Fluorine Chem. 2010, 131, 951-957
- (2010) J. Fluorine Chem. , vol.131 , pp. 951-957
- Wiehn, M.S.¹ Vinogradova, E.V.² Togni, A.³

31
- 80055074701
- references cited therein
- V. Matoušek, A. Togni, V. Bizet, D. Cahard, Org. Lett. 2011, 13, 5762-5765, and references cited therein.
- (2011) Org. Lett. , vol.13 , pp. 5762-5765
- Matoušek, V.¹ Togni, A.² Bizet, V.³ Cahard, D.⁴

32
- 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

33
- 80052851561
- Angew. Chem. Int. Ed. 2011, 50, 9120-9123
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 9120-9123

34
- 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

35
- 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

36
- 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

37
- 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

38
- 84860760651
- Angew. Chem. Int. Ed. 2012, 51, 4577-4580
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4577-4580

39
- 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

40
- 84864871408
- Angew. Chem. Int. Ed. 2012, 51, 8221-8224
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8221-8224

41
- 84868548318
- Z. He, T. Luo, M. Hu, Y. Cao, J. Hu, Angew. Chem. 2012, 124, 4010-4013
- (2012) Angew. Chem. , vol.124 , pp. 4010-4013
- He, Z.¹ Luo, T.² Hu, M.³ Cao, Y.⁴ Hu, J.⁵

42
- 84859756386
- Angew. Chem. Int. Ed. 2012, 51, 3944-3947
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3944-3947

43
- 84862908150
- 3:, X. Mu, T. Wu, H.-y. Wang, Y.-l. Guo, G. Liu, J. Am. Chem. Soc. 2012, 134, 878-881
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 878-881
- Mu, X.¹ Wu, T.² Wang, H.-Y.³ Guo, Y.-L.⁴ Liu, G.⁵

44
- 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

45
- 84875718798
- Angew. Chem. Int. Ed. 2013, 52, 4000-4003
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 4000-4003

46
- 84886638664
- E. Pair, N. Monteiro, D. Bouyssi, O. Baudoin, Angew. Chem. 2013, 125, 5454-5457
- (2013) Angew. Chem. , vol.125 , pp. 5454-5457
- Pair, E.¹ Monteiro, N.² Bouyssi, D.³ Baudoin, O.⁴

47
- 84877257777
- Angew. Chem. Int. Ed. 2013, 52, 5346-5349.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 5346-5349

48
- 84886621862
- CCDC 949953 (3 a) contains 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.

49
- 84860771111
- A. T. Parsons, T. D. Senecal, S. L. Buchwald, Angew. Chem. 2012, 124, 3001-3004
- (2012) Angew. Chem. , vol.124 , pp. 3001-3004
- Parsons, A.T.¹ Senecal, T.D.² Buchwald, S.L.³

50
- 84858221050
- Angew. Chem. Int. Ed. 2012, 51, 2947-2950.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 2947-2950

51
- 0005427983
- L. M. Yagupolskii, N. V. Kondratenko, G. N. Timofeeva, J. Org. Chem. USSR 1984, 20, 103-106
- (1984) J. Org. Chem. USSR , vol.20 , pp. 103-106
- Yagupolskii, L.M.¹ Kondratenko, N.V.² Timofeeva, G.N.³

52
- 0012262822
- T. Umemoto, S. Ishihara, J. Am. Chem. Soc. 1993, 115, 2156-2164.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 2156-2164
- Umemoto, T.¹ Ishihara, S.²

53
- 84876018896
- P. Finkbeiner, B. J. Nachtsheim, Synthesis 2013, 979-999.
- (2013) Synthesis , pp. 979-999
- Finkbeiner, P.¹ Nachtsheim, B.J.²

54
- 84886611466
- The imidoyl radical attacks the naphthyl group preferably at the ortho-position for electronic reasons, as assigned by NMR analysis. The same observations was previously reported for other imidoyl radical cyclization to the naphthyl moiety, see:, M. Tobisu, K. Koh, T. Furukawa, N. Chatani, Angew. Chem. 2012, 124, 11525-11528
- (2012) Angew. Chem. , vol.124 , pp. 11525-11528
- Tobisu, M.¹ Koh, K.² Furukawa, T.³ Chatani, N.⁴

55
- 84868109830
- Angew. Chem. Int. Ed. 2012, 51, 11363-11366.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 11363-11366

56
- 33646455332
- in (Ed.: G. Dyker), Wiley-VCH, Weinheim
- O. Porta, F. Minisci, in Handbook of C-H Transformations (Ed.:, G. Dyker,), Wiley-VCH, Weinheim, 2005, pp. 212-222.
- (2005) Handbook of C-H Transformations , pp. 212-222
- Porta, O.¹ Minisci, F.²

57
- 80052857253
- Alternatively, cyclohexadienyl radical B might act as SET-reducing reagent prior to deprotonation. See also:, A. Studer, D. P. Curran, Angew. Chem. 2011, 123, 5122-5127
- (2011) Angew. Chem. , vol.123 , pp. 5122-5127
- Studer, A.¹ Curran, D.P.²

58
- 79956102547
- Angew. Chem. Int. Ed. 2011, 50, 5018-5022.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5018-5022

59
- 84873976957
- S. Wertz, D. Leifert, A. Studer, Org. Lett. 2013, 15, 928-931.
- (2013) Org. Lett. , vol.15 , pp. 928-931
- Wertz, S.¹ Leifert, D.² Studer, A.³

60
- 22744441344
- PW6B95 functional:, Y. Zhao, D. G. Truhlar, J. Phys. Chem. A 2005, 109, 5656-5667
- (2005) J. Phys. Chem. A , vol.109 , pp. 5656-5667
- Zhao, Y.¹ Truhlar, D.G.²

61
- 77951680464
- D3 dispersion correction:, S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104
- (2010) J. Chem. Phys. , vol.132 , pp. 154104
- Grimme, S.¹ Antony, J.² Ehrlich, S.³ Krieg, H.⁴

62
- 79952943559
- S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem. 2011, 32, 1456-1465
- (2011) J. Comput. Chem. , vol.32 , pp. 1456-1465
- Grimme, S.¹ Ehrlich, S.² Goerigk, L.³

63
- 26244461462
- def2-TZVP basis set:, F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
- (2005) Phys. Chem. Chem. Phys. , vol.7 , pp. 3297-3305
- Weigend, F.¹ Ahlrichs, R.²

64
- 84961980743
- COSMO solvation model:, A. Klamt, G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799-805
- (1993) J. Chem. Soc. Perkin Trans. 2 , pp. 799-805
- Klamt, A.¹ Schüürmann, G.²

65
- 84864435917
- for free enthalpy from harmonic vibrations using a rotator approximation for low frequencies, see:, S. Grimme, Chem. Eur. J. 2012, 18, 9955-9964.
- (2012) Chem. Eur. J. , vol.18 , pp. 9955-9964
- Grimme, S.¹

66
- 33947440878
- J. F. J. Dippy, Chem. Rev. 1939, 25, 151-211.
- (1939) Chem. Rev. , vol.25 , pp. 151-211
- Dippy, J.F.J.¹

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