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Angewandte Chemie - International Edition

Volumn 51, Issue 39, 2012, Pages 9904-9908

Rhodium-catalyzed direct C-H amination of benzamides with aryl azides: A synthetic route to diarylamines

(5) Ryu, Jaeyune a Shin, Kwangmin a Park, Sae Hume a Kim, Ji Young a Chang, Sukbok a

a Korea Advanced Institute of Science and Technology (KAIST) (South Korea)

Author keywords

amination; aryl azides; C H activation; diarylamines; rhodium

Indexed keywords

ARYL AZIDES; BENZAMIDES; C-H ACTIVATION; DIARYLAMINES; HIGH YIELD; KETOXIMES; RHODIUM-CATALYZED; SYNTHETIC ROUTES;

ACTIVATION ANALYSIS; AMINATION; CATALYSIS; RHODIUM;

AMINES;

AMINE; ANILINE DERIVATIVE; AZIDE; BENZAMIDE DERIVATIVE; RHODIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

AMINATION; AMINES; ANILINE COMPOUNDS; AZIDES; BENZAMIDES; CATALYSIS; RHODIUM;

EID: 84866524518 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201205723 Document Type: Article

Times cited : (258)

References (77)

1
- 84891322438
- s, Wiley-VCH, Weinheim
- A. Ricci, Amino Group Chemistry: From Synthesis to the Life Science s, Wiley-VCH, Weinheim, 2008
- (2008) Amino Group Chemistry: From Synthesis to the Life Science
- Ricci, A.¹

2
- 28744441905
- Cambridge University Press, Cambridge
- S. A. Lawrence, Amines: Synthesis Properties and Applications, Cambridge University Press, Cambridge, 2004.
- (2004) Amines: Synthesis Properties and Applications
- Lawrence, S.A.¹

3
- 33750322985
- T. Suzuki, K. Imai, H. Nakagawa, N. Miyata, ChemMedChem 2006, 1, 1059
- (2006) ChemMedChem , vol.1 , pp. 1059
- Suzuki, T.¹ Imai, K.² Nakagawa, H.³ Miyata, N.⁴

4
- 68149145658
- T. Suzuki, K. Imai, E. Imai, S. lida, R. Ueda, H. Tsumoto, H. Nakagawa, N. Miyata, Bioorg. Med. Chem. 2009, 17, 5900
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 5900
- Suzuki, T.¹ Imai, K.² Imai, E.³ Lida, S.⁴ Ueda, R.⁵ Tsumoto, H.⁶ Nakagawa, H.⁷ Miyata, N.⁸

5
- 84861017745
- et al
- K. D. Rice, et al., ACS Med. Chem. Lett. 2012, 3, 416.
- (2012) ACS Med. Chem. Lett. , vol.3 , pp. 416
- Rice, K.D.¹

6
- 0032970177
- P. W. Baures, V. B. Oza, S. A. Peterson, J. W. Kelly, Bioorg. Med. Chem. 1999, 7, 1339
- (1999) Bioorg. Med. Chem. , vol.7 , pp. 1339
- Baures, P.W.¹ Oza, V.B.² Peterson, S.A.³ Kelly, J.W.⁴

7
- 29744441083
- C. Cougiu, M. T. Cocco, V. Lilliiu, V. Onnis, J. Med. Chem. 2005, 48, 8245
- (2005) J. Med. Chem. , vol.48 , pp. 8245
- Cougiu, C.¹ Cocco, M.T.² Lilliiu, V.³ Onnis, V.⁴

8
- 84863230589
- A. O. Adeniji, B. M. Twenter, M. C. Byrns, Y. Jin, M. Chen, J. D. Winkler, T. M. Penning, J. Med. Chem. 2012, 55, 2311.
- (2012) J. Med. Chem. , vol.55 , pp. 2311
- Adeniji, A.O.¹ Twenter, B.M.² Byrns, M.C.³ Jin, Y.⁴ Chen, M.⁵ Winkler, J.D.⁶ Penning, T.M.⁷

9
- 0014354867
- W. E. Coyne, J. W. Cusic, J. Med. Chem. 1968, 11, 1208
- (1968) J. Med. Chem. , vol.11 , pp. 1208
- Coyne, W.E.¹ Cusic, J.W.²

10
- 84988109283
- L. Baiocchi, G. Corsi, G. Palazzo, Synthesis 1978, 633
- (1978) Synthesis , pp. 633
- Baiocchi, L.¹ Corsi, G.² Palazzo, G.³

11
- 0142029714
- K. Ozaki, Y. Yamada, T. Oine, J. Org. Chem. 1981, 46, 1571
- (1981) J. Org. Chem. , vol.46 , pp. 1571
- Ozaki, K.¹ Yamada, Y.² Oine, T.³

12
- 0038654691
- G. P. Moloney, D. P. Kelly, P. Mack, Molecules 2001, 6, 230
- (2001) Molecules , vol.6 , pp. 230
- Moloney, G.P.¹ Kelly, D.P.² MacK, P.³

13
- 0036645871
- H. Koshima, K. Kutsunai, Heterocycles 2002, 57, 1299
- (2002) Heterocycles , vol.57 , pp. 1299
- Koshima, H.¹ Kutsunai, K.²

14
- 84860624351
- A. W. Schmidt, K. R. Reddy, H.-J. Knölker, Chem. Rev. 2012, 112, 3193.
- (2012) Chem. Rev. , vol.112 , pp. 3193
- Schmidt, A.W.¹ Reddy, K.R.² Knölker, H.-J.³

15
- 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

16
- 0003034786
- M. Kosugi, M. Kameyama, T. Migita, Chem. Lett. 1983, 12, 927.
- (1983) Chem. Lett. , vol.12 , pp. 927
- Kosugi, M.¹ Kameyama, M.² Migita, T.³

17
- 33747073729
- A. S. Guram, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 7901
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 7901
- Guram, A.S.¹ Buchwald, S.L.²

18
- 0000499068
- F. Paul, J. Patt, J. F. Hartwig, J. Am. Chem. Soc. 1994, 116, 5969.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 5969
- Paul, F.¹ Patt, J.² Hartwig, J.F.³

19
- 78149463267
- A. Armstrong, J. C. Collins, Angew. Chem. 2010, 122, 2332
- (2010) Angew. Chem. , vol.122 , pp. 2332
- Armstrong, A.¹ Collins, J.C.²

20
- 77952879070
- Angew. Chem. Int. Ed. 2010, 49, 2282
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2282

21
- 80054105790
- J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
- (2011) Chem. Soc. Rev. , vol.40 , pp. 4740
- Wencel-Delord, J.¹ Dröge, T.² Liu, F.³ Glorius, F.⁴

22
- 80054728269
- S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068.
- (2011) Chem. Soc. Rev. , vol.40 , pp. 5068
- Cho, S.H.¹ Kim, J.Y.² Kwak, J.³ Chang, S.⁴

23
- 70749147617
- Q. Wang, S. L. Schreiber, Org. Lett. 2009, 11, 5178
- (2009) Org. Lett. , vol.11 , pp. 5178
- Wang, Q.¹ Schreiber, S.L.²

24
- 64349114690
- D. Monguchi, T. Fujiwara, H. Furukawa, A. Mori, Org. Lett. 2009, 11, 1607
- (2009) Org. Lett. , vol.11 , pp. 1607
- Monguchi, D.¹ Fujiwara, T.² Furukawa, H.³ Mori, A.⁴

25
- 84856086615
- For the oxidative direct amination of arenes containing chelating groups, see
- Y. Oda, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2012, 14, 664. For the oxidative direct amination of arenes containing chelating groups, see
- (2012) Org. Lett. , vol.14 , pp. 664
- Oda, Y.¹ Hirano, K.² Satoh, T.³ Miura, M.⁴

26
- 33744786786
- X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 6790
- Chen, X.¹ Hao, X.-S.² Goodhue, C.E.³ Yu, J.-Q.⁴

27
- 33746071928
- H.-Y. Thu, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2006, 128, 9048
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 9048
- Thu, H.-Y.¹ Yu, W.-Y.² Che, C.-M.³

28
- 79551712208
- B. Xiao, T.-J. Gong, J. Xu, Z.-J. Liu, L. Liu, J. Am. Chem. Soc. 2011, 133, 1466
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 1466
- Xiao, B.¹ Gong, T.-J.² Xu, J.³ Liu, Z.-J.⁴ Liu, L.⁵

29
- 79956072566
- A. John, K. M. Nicholas, J. Org. Chem. 2011, 76, 4158
- (2011) J. Org. Chem. , vol.76 , pp. 4158
- John, A.¹ Nicholas, K.M.²

30
- 79952638920
- B. Haffemayer, M. Gulias, M. J. Gaunt, Chem. Sci. 2011, 2, 312
- (2011) Chem. Sci. , vol.2 , pp. 312
- Haffemayer, B.¹ Gulias, M.² Gaunt, M.J.³

31
- 79960488436
- J. Du Bois, Org. Process Res. Dev. 2011, 15, 758.
- (2011) Org. Process Res. Dev. , vol.15 , pp. 758
- Du Bois, J.¹

32
- 77952559474
- T. Kawano, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2010, 132, 6900
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 6900
- Kawano, T.¹ Hirano, K.² Satoh, T.³ Miura, M.⁴

33
- 77956620860
- K.-H. Ng, A. S. C. Chan, W.-Y. Yu, J. Am. Chem. Soc. 2010, 132, 12862
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 12862
- Ng, K.-H.¹ Chan, A.S.C.² Yu, W.-Y.³

34
- 79951532301
- K. Sun, Y. Li, T. Xiong, J. Zhang, Q. Zhang, J. Am. Chem. Soc. 2011, 133, 1694
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 1694
- Sun, K.¹ Li, Y.² Xiong, T.³ Zhang, J.⁴ Zhang, Q.⁵

35
- 79957699837
- E. J. Yoo, S. Ma, T.-S. Mei, K. S. L. Chan, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 7652
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 7652
- Yoo, E.J.¹ Ma, S.² Mei, T.-S.³ Chan, K.S.L.⁴ Yu, J.-Q.⁵

36
- 84862908591
- K.-H. Ng, Z. Zhou, W.-Y. Yu, Org. Lett. 2012, 14, 272
- (2012) Org. Lett. , vol.14 , pp. 272
- Ng, K.-H.¹ Zhou, Z.² Yu, W.-Y.³

37
- 84862908348
- C. Grohmann, H. Wang, F. Glorius, Org. Lett. 2012, 14, 656.
- (2012) Org. Lett. , vol.14 , pp. 656
- Grohmann, C.¹ Wang, H.² Glorius, F.³

38
- 79960226569
- J. Y. Kim, S. H. Cho, J. Joseph, S. Chang, Angew. Chem. 2010, 122, 10095
- (2010) Angew. Chem. , vol.122 , pp. 10095
- Kim, J.Y.¹ Cho, S.H.² Joseph, J.³ Chang, S.⁴

39
- 78650279320
- Angew. Chem. Int. Ed. 2010, 49, 9899
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 9899

40
- 77950197548
- M. Kim, S. Chang, Org. Lett. 2010, 12, 1640
- (2010) Org. Lett. , vol.12 , pp. 1640
- Kim, M.¹ Chang, S.²

41
- 80054764821
- H. J. Kim, J. Kim, S. H. Cho, S. Chang, J. Am. Chem. Soc. 2011, 133, 16382
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 16382
- Kim, H.J.¹ Kim, J.² Cho, S.H.³ Chang, S.⁴

42
- 79954555813
- S. H. Cho, J. Yoon, S. Chang, J. Am. Chem. Soc. 2011, 133, 5996.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 5996
- Cho, S.H.¹ Yoon, J.² Chang, S.³

43
- 84861841569
- J. Y. Kim, S. H. Park, J. Ryu, S. H. Cho, S. H. Kim, S. Chang, J. Am. Chem. Soc. 2012, 134, 9110.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 9110
- Kim, J.Y.¹ Park, S.H.² Ryu, J.³ Cho, S.H.⁴ Kim, S.H.⁵ Chang, S.⁶

44
- 27944494395
- S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320
- (2005) Angew. Chem. , vol.117 , pp. 5320
- Bräse, S.¹ Gil, C.² Knepper, K.³ Zimmermann, V.⁴

45
- 24044531286
- Angew. Chem. Int. Ed. 2005, 44, 5188.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5188

46
- 29344457003
- T. Katsuki, Chem. Lett. 2005, 34, 1304
- (2005) Chem. Lett. , vol.34 , pp. 1304
- Katsuki, T.¹

47
- 33747052051
- S. Cenini, E. Gallo, A. Caselli, F. Ragaini, S. Fantauzzi, C. Piangiolino, Coord. Chem. Rev. 2006, 250, 1234
- (2006) Coord. Chem. Rev. , vol.250 , pp. 1234
- Cenini, S.¹ Gallo, E.² Caselli, A.³ Ragaini, F.⁴ Fantauzzi, S.⁵ Piangiolino, C.⁶

48
- 77955475317
- T. G. Driver, Org. Biomol. Chem. 2010, 8, 3831.
- (2010) Org. Biomol. Chem. , vol.8 , pp. 3831
- Driver, T.G.¹

49
- 34250851338
- B. J. Stokes, H. Dong, B. E. Leslie, A. L. Pumphrey, T. G. Driver, J. Am. Chem. Soc. 2007, 129, 7500
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 7500
- Stokes, B.J.¹ Dong, H.² Leslie, B.E.³ Pumphrey, A.L.⁴ Driver, T.G.⁵

50
- 73549122997
- W. G. Shou, J. Li, T. Guo, Z. Lin, G. Jia, Organometallics 2009, 28, 6847
- (2009) Organometallics , vol.28 , pp. 6847
- Shou, W.G.¹ Li, J.² Guo, T.³ Lin, Z.⁴ Jia, G.⁵

51
- 79955377801
- J. Bonnamour, C. Bolm, Org. Lett. 2011, 13, 2012
- (2011) Org. Lett. , vol.13 , pp. 2012
- Bonnamour, J.¹ Bolm, C.²

52
- 84860823917
- Q. Nguyen, K. Sun, T. G. Driver, J. Am. Chem. Soc. 2012, 134, 7262.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 7262
- Nguyen, Q.¹ Sun, K.² Driver, T.G.³

53
- 0034700227
- S. Cenini, E. Gallo, A. Penoni, F. Ragaini, S. Tollari, Chem. Commun. 2000, 2265
- (2000) Chem. Commun. , pp. 2265
- Cenini, S.¹ Gallo, E.² Penoni, A.³ Ragaini, F.⁴ Tollari, S.⁵

54
- 71749090844
- Y. M. Badiei, A. Dinescu, X. Dai, R. M. Palomino, F. W. Heinemann, T. R. Cundari, T. H. Warren, Angew. Chem. 2008, 120, 10109
- (2008) Angew. Chem. , vol.120 , pp. 10109
- Badiei, Y.M.¹ Dinescu, A.² Dai, X.³ Palomino, R.M.⁴ Heinemann, F.W.⁵ Cundari, T.R.⁶ Warren, T.H.⁷

55
- 57549106843
- Angew. Chem. Int. Ed. 2008, 47, 9961.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9961

56
- 79955025786
- Y.-F. Wang, K. K. Toh, E. P. J. Ng, S. Chiba, J. Am. Chem. Soc. 2011, 133, 6411
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 6411
- Wang, Y.-F.¹ Toh, K.K.² Ng, E.P.J.³ Chiba, S.⁴

57
- 81755174471
- Y.-F. Wang, K. K. Toh, J.-Y. Lee, S. Chiba, Angew. Chem. 2011, 123, 6049
- (2011) Angew. Chem. , vol.123 , pp. 6049
- Wang, Y.-F.¹ Toh, K.K.² Lee, J.-Y.³ Chiba, S.⁴

58
- 79959248591
- Angew. Chem. Int. Ed. 2011, 50, 5927.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5927

59
- 77949833507
- Q. Shuai, G. Deng, Z. Chua, D. S. Bohle, C.-J. Li, Adv. Synth. Catal. 2010, 352, 632
- (2010) Adv. Synth. Catal. , vol.352 , pp. 632
- Shuai, Q.¹ Deng, G.² Chua, Z.³ Bohle, D.S.⁴ Li, C.-J.⁵

60
- 80051699705
- X.-Y. Liu, P. Gao, Y.-W. Shen, Y.-M. Liang, Org. Lett. 2011, 13, 4196.
- (2011) Org. Lett. , vol.13 , pp. 4196
- Liu, X.-Y.¹ Gao, P.² Shen, Y.-W.³ Liang, Y.-M.⁴

61
- 79959744411
- L. Ackermann, A. V. Lygin, Org. Lett. 2011, 13, 3332.
- (2011) Org. Lett. , vol.13 , pp. 3332
- Ackermann, L.¹ Lygin, A.V.²

62
- 84863668849
- E. M. Simmons, J. F. Hartwig, Angew. Chem. 2012, 124, 3120
- (2012) Angew. Chem. , vol.124 , pp. 3120
- Simmons, E.M.¹ Hartwig, J.F.²

63
- 84858776560
- Angew. Chem. Int. Ed. 2012, 51, 3066.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3066

64
- 51949093660
- L. Li, W. W. Brennessel, W. D. Jones, J. Am. Chem. Soc. 2008, 130, 12414.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 12414
- Li, L.¹ Brennessel, W.W.² Jones, W.D.³

65
- 0038321455
- I. Nägeli, C. Baud, G. Bernardinelli, Y. Jacquier, M. Moran, P. Müller, Helv. Chim. Acta 1997, 80, 1087
- (1997) Helv. Chim. Acta , vol.80 , pp. 1087
- Nägeli, I.¹ Baud, C.² Bernardinelli, G.³ Jacquier, Y.⁴ Moran, M.⁵ Müller, P.⁶

66
- 38749146550
- H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417
- (2008) Nature , vol.451 , pp. 417
- Davies, H.M.L.¹ Manning, J.R.²

67
- 84866518930
- N. Jung, S. Bräse, Angew. Chem. 2012, 124, 5632
- (2012) Angew. Chem. , vol.124 , pp. 5632
- Jung, N.¹ Bräse, S.²

68
- 84861589637
- Angew. Chem. Int. Ed. 2012, 51, 5538.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 5538

69
- 84861399854
- N. Schröder, J. Wencel-Delord, F. Glorius, J. Am. Chem. Soc. 2012, 134, 8298
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 8298
- Schröder, N.¹ Wencel-Delord, J.² Glorius, F.³

70
- 84861515205
- J. Wencel-Delord, C. Nimphius, F. W. Patureau, F. Glorius, Angew. Chem. 2012, 124, 2290
- (2012) Angew. Chem. , vol.124 , pp. 2290
- Wencel-Delord, J.¹ Nimphius, C.² Patureau, F.W.³ Glorius, F.⁴

71
- 84857522039
- Angew. Chem. Int. Ed. 2012, 51, 2247.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 2247

72
- 46849109148
- B. Liégault, D. Lee, M. P. Huestis, D. R. Stuart, K. Fagnou, J. Org. Chem. 2008, 73, 5022.
- (2008) J. Org. Chem. , vol.73 , pp. 5022
- Liégault, B.¹ Lee, D.² Huestis, M.P.³ Stuart, D.R.⁴ Fagnou, K.⁵

73
- 84866495110
- see also, ref [10d]
- G. G. Tokmadzhyan, Russ. J. Org. Chem. 2011, 47, 1708; see also, ref [10d].
- (2011) Russ. J. Org. Chem. , vol.47 , pp. 1708
- Tokmadzhyan, G.G.¹

74
- 0014346110
- G. Zoni, G. Picciola, Boll. Chim. Farm. 1968, 107, 598
- (1968) Boll. Chim. Farm. , vol.107 , pp. 598
- Zoni, G.¹ Picciola, G.²

75
- 0015016247
- G. Zoni, M. L. Molinari, Boll. Chim. Farm. 1971, 110, 105.
- (1971) Boll. Chim. Farm. , vol.110 , pp. 105
- Zoni, G.¹ Molinari, M.L.²

76
- 79953173901
- H. V. Le, L. Fan, B. Ganem, Tetrahedron Lett. 2011, 52, 2209.
- (2011) Tetrahedron Lett. , vol.52 , pp. 2209
- Le, H.V.¹ Fan, L.² Ganem, B.³

77
- 33847675454
- E. Takács, C. Varga, R. Skoda-Földes, L. Kollár, Tetrahedron Lett. 2007, 48, 2453.
- (2007) Tetrahedron Lett. , vol.48 , pp. 2453
- Takács, E.¹ Varga, C.² Skoda-Földes, R.³ Kollár, L.⁴

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