SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 51, Issue 52, 2012, Pages 13070-13074

Pd-catalyzed C-H oxygenation with TFA/TFAA: Expedient access to oxygen-containing heterocycles and late-stage drug modification

(4) Shan, Gang a Yang, Xinglin a Ma, Linlin a Rao, Yu a

a Tsinghua University (China)

Author keywords

C H activation; Drug modification; Hydroxylation; Palladium; Phenol synthesis

Indexed keywords

ACEBUTOLOL; AROMATIC HALIDE; AROMATIC KETONES; BENZOXAZOLE; BENZYLIC ALCOHOLS; BUILDING BLOCKES; C-H ACTIVATION; C-H FUNCTIONALIZATION; CHEMO-SELECTIVITY; CHEMOSELECTIVE; DEMETHYLATION; DIRECT HYDROXYLATION; DRUG MODIFICATION; FRIES REARRANGEMENT; FUNCTIONALIZED; HETEROCYCLES; LOW-YIELD; METHYL PHENYL ETHERS; PHENOL SYNTHESIS; REACTION CONDITIONS; SIDE PRODUCTS; SYNTHETIC INTERMEDIATES;

ACTIVATION ANALYSIS; AGRICULTURAL CHEMICALS; AROMATIZATION; CATALYSIS; HYDROXYLATION; KETONES; ORGANIC COMPOUNDS; OXYGEN; OXYGENATION; PALLADIUM; PHENOLS; TRANSITION METALS;

SYNTHESIS (CHEMICAL);

ACETIC ANHYDRIDE; CARBON; FLUOROACETIC ACID; HETEROCYCLIC COMPOUND; HYDROGEN; OXYGEN; PALLADIUM; TRIFLUOROACETIC ACID; TRIFLUOROACETIC ANHYDRIDE;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ACETIC ANHYDRIDES; CARBON; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; FLUOROACETATES; HETEROCYCLIC COMPOUNDS; HYDROGEN; MOLECULAR CONFORMATION; OXYGEN; PALLADIUM; STEREOISOMERISM; TRIFLUOROACETIC ACID;

EID: 84871956213 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201207458 Document Type: Article

Times cited : (248)

References (70)

1
- 0003904089
- Elsevier, New York
- J. H. P. Tyman, Synthetic and Natural Phenols, Elsevier, New York, 1996
- (1996) Synthetic and Natural Phenols
- Tyman, J.H.P.¹

2
- 0345736841
- Wiley-VCH, Weinheim
- Z. Rappoport, The Chemistry of Phenols, Wiley-VCH, Weinheim, 2003
- (2003) The Chemistry of Phenols
- Rappoport, Z.¹

3
- 4444333382
- Wiley-Interscience, New York
- J. F. Hartwig, Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1, Wiley-Interscience, New York, 2002, p. 1097
- (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.1 , pp. 1097
- Hartwig, J.F.¹

4
- 0142109734
- R. B. Bedford, S. J. Coles, M. B. Hursthouse,M. E. Limmert, Angew. Chem. 2003, 115, 116
- (2003) Angew. Chem. , vol.115 , pp. 116
- Bedford, R.B.¹ Coles, S.J.² Hursthouse, M.B.³ Limmert, M.E.⁴

5
- 0347296197
- Angew. Chem. Int. Ed. 2003, 42, 112
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 112

6
- 0037459413
- R. Dorta, A. Tongi, Chem. Commun. 2003, 760
- (2003) Chem. Commun. , vol.760
- Dorta, R.¹ Tongi, A.²

7
- 45249114139
- T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 7534.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 7534
- Boebel, T.A.¹ Hartwig, J.F.²

8
- 15244350902
- P. J. Alaimo, Z. A. Knight, K. M. Shokat, Bioorg. Med. Chem. 2005, 13, 2825.
- (2005) Bioorg. Med. Chem. , vol.13 , pp. 2825
- Alaimo, P.J.¹ Knight, Z.A.² Shokat, K.M.³

9
- 79953189669
- H. Xu, Y. Liang, Z. Cai, H. Qi, C. Yang, Y. Feng, J. Org. Chem. 2011, 76, 2296.
- (2011) J. Org. Chem. , vol.76 , pp. 2296
- Xu, H.¹ Liang, Y.² Cai, Z.³ Qi, H.⁴ Yang, C.⁵ Feng, Y.⁶

10
- 0000418439
- J. A. Miller, J. Org. Chem. 1987, 52, 322.
- (1987) J. Org. Chem. , vol.52 , pp. 322
- Miller, J.A.¹

11
- 0034364865
- J. S. Yadav, B. V. S. Reddy, Ch. Madan, S. R. Hashim, Chem. Lett. 2000, 738.
- (2000) Chem. Lett. , pp. 738
- Yadav, J.S.¹ Reddy, B.V.S.² Madan, C.³ Hashim, S.R.⁴

12
- 0242526099
- For general reviews on the transition-metal-catalyzed C-H activation of arenes
- For general reviews on the transition-metal-catalyzed C-H activation of arenes, see: F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077
- (2003) Adv. Synth. Catal. , vol.345 , pp. 1077
- Kakiuchi, F.¹ Chatani, N.²

13
- 32644440329
- A. R. Dick, M. S. Sanford, Tetrahedron 2006, 62, 2439
- (2006) Tetrahedron , vol.62 , pp. 2439
- Dick, A.R.¹ Sanford, M.S.²

14
- 33645674829
- K. Godula, D. Sames, Science 2006, 312, 67
- (2006) Science , vol.312 , pp. 67
- Godula, K.¹ Sames, D.²

15
- 33750509858
- J. Q. Yu, R. Giri, X. Chen, Org. Biomol. Chem. 2006, 4, 4041
- (2006) Org. Biomol. Chem. , vol.4 , pp. 4041
- Yu, J.Q.¹ Giri, R.² Chen, X.³

16
- 33846918696
- D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
- (2007) Chem. Rev. , vol.107 , pp. 174
- Alberico, D.¹ Scott, M.E.² Lautens, M.³

17
- 77949410036
- L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
- (2009) Angew. Chem. , vol.121 , pp. 9976
- Ackermann, L.¹ Vicente, R.² Kapdi, A.R.³

18
- 72449170089
- Angew. Chem. Int. Ed. 2009, 48, 9792
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9792

19
- 68949185025
- O. Daugulis, H. Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
- (2009) Acc. Chem. Res. , vol.42 , pp. 1074
- Daugulis, O.¹ Do, H.Q.² Shabashov, D.³

20
- 77349090183
- D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
- (2010) Chem. Rev. , vol.110 , pp. 624
- Colby, D.A.¹ Bergman, R.G.² Ellman, J.A.³

21
- 77949381429
- T.W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
- (2010) Chem. Rev. , vol.110 , pp. 1147
- Lyons, T.W.¹ Sanford, M.S.²

22
- 75749111062
- L.-M. Xu, B.-J. Li, Z. Yang, Z. J. Shi, Chem. Soc. Rev. 2010, 39, 712.
- (2010) Chem. Soc. Rev. , vol.39 , pp. 712
- Xu, L.-M.¹ Li, B.-J.² Yang, Z.³ Shi, Z.J.⁴

23
- 80054999158
- For illustrative examples of the transition-metal-catalyzed C-H activation of arenes
- For illustrative examples of the transition-metal-catalyzed C-H activation of arenes, see: S. Enthaler, A. Company, Chem. Soc. Rev. 2011, 40, 4912
- (2011) Chem. Soc. Rev. , vol.40 , pp. 4912
- Enthaler, S.¹ Company, A.²

24
- 1542345322
- A. R. Dick, K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2004, 126, 2300
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 2300
- Dick, A.R.¹ Hull, K.L.² Sanford, M.S.³

25
- 77953624806
- N. Chernyak, A. S. Dudnik, C. Huang, V. Gevorgyan, J. Am. Chem. Soc. 2010, 132, 8270
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 8270
- Chernyak, N.¹ Dudnik, A.S.² Huang, C.³ Gevorgyan, V.⁴

26
- 33646456189
- L. V. Desai, H. A. Malik, M. S. Sanford, Org. Lett. 2006, 8, 1141
- (2006) Org. Lett. , vol.8 , pp. 1141
- Desai, L.V.¹ Malik, H.A.² Sanford, M.S.³

27
- 72849149530
- F. R. Gou, X. C. Wang, P. F. Huo, H. P. Bi, Z. H. Guan, Y. M. Liang, Org. Lett. 2009, 11, 5726
- (2009) Org. Lett. , vol.11 , pp. 5726
- Gou, F.R.¹ Wang, X.C.² Huo, P.F.³ Bi, H.P.⁴ Guan, Z.H.⁵ Liang, Y.M.⁶

28
- 77955367873
- X. Zheng, B. Song, B. Xu, Eur. J. Org. Chem. 2010, 4376
- (2010) Eur. J. Org. Chem. , pp. 4376
- Zheng, X.¹ Song, B.² Xu, B.³

29
- 75349099607
- G.W. Wang, T. T. Yuan, J. Org. Chem. 2010, 75, 476
- (2010) J. Org. Chem. , vol.75 , pp. 476
- Wang, G.W.¹ Yuan, T.T.²

30
- 33745922538
- R. Giri, J. Liang, J.-G. Lei, J.-J. Li, D.-H.Wang, X. Chen, I. C. Naggar, C. Guo, B. M. Foxman, J.-Q. Yu, Angew. Chem. 2005, 117, 7586
- (2005) Angew. Chem. , vol.117 , pp. 7586
- Giri, R.¹ Liang, J.² Lei, J.-G.³ Li, J.-J.⁴ Wang, D.-H.⁵ Chen, X.⁶ Naggar, I.C.⁷ Guo, C.⁸ Foxman, B.M.⁹ Yu, J.-Q.¹⁰

31
- 28044468663
- Angew. Chem. Int. Ed. 2005, 44, 7420.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 7420

32
- 25144474992
- A. R. Dick, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 12790
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 12790
- Dick, A.R.¹ Kampf, J.W.² Sanford, M.S.³

33
- 33646107383
- E. W. Kalberer, S. R. Whitfield, M. S. Sanford, J. Mol. Catal. A 2006, 251, 108
- (2006) J. Mol. Catal. A , vol.251 , pp. 108
- Kalberer, E.W.¹ Whitfield, S.R.² Sanford, M.S.³

34
- 34047101384
- N. R. Deprez, M. S. Sanford, Inorg. Chem. 2007, 46, 1924
- (2007) Inorg. Chem. , vol.46 , pp. 1924
- Deprez, N.R.¹ Sanford, M.S.²

35
- 75749134825
- S. R. Neufeldt, M. S. Sanford, Org. Lett. 2010, 12, 532
- (2010) Org. Lett. , vol.12 , pp. 532
- Neufeldt, S.R.¹ Sanford, M.S.²

36
- 0002776509
- T. Jintoku, K. Nishimura, K. Takaki, Y. Fujiwara, Chem. Lett. 1990, 1687
- (1990) Chem. Lett. , pp. 1687
- Jintoku, T.¹ Nishimura, K.² Takaki, K.³ Fujiwara, Y.⁴

37
- 79959240201
- B. Xiao, T. J. Gong, Z. J. Liu, J. H. Liu, D. F. Luo, J. Xu, L. Liu, J. Am. Chem. Soc. 2011, 133, 9250
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 9250
- Xiao, B.¹ Gong, T.J.² Liu, Z.J.³ Liu, J.H.⁴ Luo, D.F.⁵ Xu, J.⁶ Liu, L.⁷

38
- 80455129314
- C. H. Huang, N. Ghavtadze, B. Chattopadhyay, V. Gevorgyan, J. Am. Chem. Soc. 2011, 133, 17630
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 17630
- Huang, C.H.¹ Ghavtadze, N.² Chattopadhyay, B.³ Gevorgyan, V.⁴

39
- 0037016398
- S. I. Niwa, M. Eswaramoorthy, J. Nair, A. Raj, N. Itoh, H. Shoji, T. Namba, F. Mizukami, Science 2002, 295, 105.
- (2002) Science , vol.295 , pp. 105
- Niwa, S.I.¹ Eswaramoorthy, M.² Nair, J.³ Raj, A.⁴ Itoh, N.⁵ Shoji, H.⁶ Namba, T.⁷ Mizukami, F.⁸

40
- 77953892735
- P. Gandeepan, K. Parthasarathy, C. Cheng, J. Am. Chem. Soc. 2010, 132, 8569
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 8569
- Gandeepan, P.¹ Parthasarathy, K.² Cheng, C.³

41
- 79551712208
- B. Xiao, T. Gong, J. Xu, Z. Liu, L. Liu, J. Am. Chem. Soc. 2011, 133, 1466
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 1466
- Xiao, B.¹ Gong, T.² Xu, J.³ Liu, Z.⁴ Liu, L.⁵

42
- 79955691468
- H.-X. Dai, A. F. Stepan, M. S. Plummer, Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 7222
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 7222
- Dai, H.-X.¹ Stepan, A.F.² Plummer, M.S.³ Zhang, Y.-H.⁴ Yu, J.-Q.⁵

43
- 70350052779
- Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 14654
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 14654
- Zhang, Y.-H.¹ Yu, J.-Q.²

44
- 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

45
- 0000037010
- M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211.
- (1998) J. Org. Chem. , vol.63 , pp. 5211
- Miura, M.¹ Tsuda, T.² Satoh, T.³ Pivsa-Art, S.⁴ Nomura, M.⁵

46
- 84863446276
- For C-H activation through weak coordination
- For C-H activation through weak coordination, see: K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
- (2012) Acc. Chem. Res. , vol.45 , pp. 788
- Engle, K.M.¹ Mei, T.-S.² Wasa, M.³ Yu, J.-Q.⁴

47
- 80755137037
- K. M. Engle, P. S. Thuy-Boun, M. Dang, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 18183
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 18183
- Engle, K.M.¹ Thuy-Boun, P.S.² Dang, M.³ Yu, J.-Q.⁴

48
- 54849420705
- R. Giri, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 14082
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14082
- Giri, R.¹ Yu, J.-Q.²

49
- 33746918323
- D.-H. Wang, D.-F. Wu, J.-Q. Yu, Org. Lett. 2006, 8, 3387
- (2006) Org. Lett. , vol.8 , pp. 3387
- Wang, D.-H.¹ Wu, D.-F.² Yu, J.-Q.³

50
- 77951186891
- Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, Angew. Chem. 2009, 121, 6213
- (2009) Angew. Chem. , vol.121 , pp. 6213
- Zhang, Y.-H.¹ Shi, B.-F.² Yu, J.-Q.³

51
- 70349777759
- Angew. Chem. Int. Ed. 2009, 48, 6097.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6097

52
- 25444475266
- D. Kalyani, M. S. Sanford, Org. Lett. 2005, 7, 4149.
- (2005) Org. Lett. , vol.7 , pp. 4149
- Kalyani, D.¹ Sanford, M.S.²

53
- 79960914042
- For other F+ oxidants
- For other F+ oxidants, see: K. M. Engle, T.-S. Mei, X.Wang, J.-Q. Yu, Angew. Chem. 2011, 123, 1514
- (2011) Angew. Chem. , vol.123 , pp. 1514
- Engle, K.M.¹ Mei, T.-S.² Wang, X.³ Yu, J.-Q.⁴

54
- 79851471855
- Angew. Chem. Int. Ed. 2011, 50, 1478
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 1478

55
- 77956233002
- X. Wang, Y. Lu, H. X. Dai, J. Q. Yu, J. Am. Chem. Soc. 2010, 132, 12203
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 12203
- Wang, X.¹ Lu, Y.² Dai, H.X.³ Yu, J.Q.⁴

56
- 77953003469
- C. Vickers, T.-S. Mei, J.-Q. Yu, Org. Lett. 2010, 12, 2511.
- (2010) Org. Lett. , vol.12 , pp. 2511
- Vickers, C.¹ Mei, T.-S.² Yu, J.-Q.³

57
- 84862908407
- H. Dai, J. Yu, J. Am. Chem. Soc. 2012, 134, 134.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 134
- Dai, H.¹ Yu, J.²

58
- 84871977727
- U.S. Pat. Appl. Publ. US 20110250250A1 20111013
- S. Kishida, Y. Kawasaki, R. Yakupcin, U.S. Pat. Appl. Publ. US 20110250250A1 20111013, 2011.
- (2011)
- Kishida, S.¹ Kawasaki, Y.² Yakupcin, R.³

59
- 77957024031
- B. Djavan, M. J. Handl, S. Dianat, Expert Opin. Pharmacother. 2010, 11, 2535.
- (2010) Expert Opin. Pharmacother. , vol.11 , pp. 2535
- Djavan, B.¹ Handl, M.J.² Dianat, S.³

60
- 34047185373
- M. Cabrera, M. Simoens, G. Falchi, M. L. Lavaggi, O. E. Piro, E. E. Castellano, A. Vidal, A. Azqueta, A. Monge, A. L. D. Cerain, G. Sagrera, G. Seoane, H. Cerecetto, M. Gonzalez, Bioorg. Med. Chem. 2007, 15, 3356
- (2007) Bioorg. Med. Chem. , vol.15 , pp. 3356
- Cabrera, M.¹ Simoens, M.² Falchi, G.³ Lavaggi, M.L.⁴ Piro, O.E.⁵ Castellano, E.E.⁶ Vidal, A.⁷ Azqueta, A.⁸ Monge, A.⁹ Cerain, A.L.D.¹⁰ Sagrera, G.¹¹ Seoane, G.¹² Cerecetto, H.¹³ Gonzalez, M.¹⁴

61
- 0347624001
- J.W. Coe,M. G. Vetelino, J. Org. Chem. 2003, 68, 9964
- (2003) J. Org. Chem. , vol.68 , pp. 9964
- Coe, J.W.¹ Vetelino, M.G.²

62
- 67149108356
- N. Barbero, R. SanMartin, E. Dominguez, Tetrahedron 2009, 65, 5729
- (2009) Tetrahedron , vol.65 , pp. 5729
- Barbero, N.¹ Sanmartin, R.² Dominguez, E.³

63
- 84869075629
- M. Moure, R. SanMartin, E. Dominguez, Angew. Chem. 2012, 124, 3274
- (2012) Angew. Chem. , vol.124 , pp. 3274
- Moure, M.¹ Sanmartin, R.² Dominguez, E.³

64
- 84858786722
- Angew. Chem. Int. Ed. 2012, 51, 3220
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3220

65
- 82355168550
- C. Chen, T. Andreani, H. Li, Org. Lett. 2011, 13, 6300
- (2011) Org. Lett. , vol.13 , pp. 6300
- Chen, C.¹ Andreani, T.² Li, H.³

66
- 34247226146
- H. Miyake, A. Nishimura, M. Yago, M. Sasaki, Chem. Lett. 2007, 36, 332
- (2007) Chem. Lett. , vol.36 , pp. 332
- Miyake, H.¹ Nishimura, A.² Yago, M.³ Sasaki, M.⁴

67
- 80052559866
- D. Tsvelikhovsky, S. L. Buchwald, J. Am. Chem. Soc. 2011, 133, 14228.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 14228
- Tsvelikhovsky, D.¹ Buchwald, S.L.²

68
- 0030464824
- For methane C-H oxygenation examples
- For methane C-H oxygenation examples, see: N. Basickes, T. E. Hogan, A. Sen, J. Am. Chem. Soc. 1996, 118, 13111
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 13111
- Basickes, N.¹ Hogan, T.E.² Sen, A.³

69
- 33749115452
- L. Kao, A. C. Hutson, A. Sen, J. Am. Chem. Soc. 1991, 113, 700.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 700
- Kao, L.¹ Hutson, A.C.² Sen, A.³

70
- 80755123500
- J. M. Racowski, N. D. Ball, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18022.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 18022
- Racowski, J.M.¹ Ball, N.D.² Sanford, M.S.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.