SCOPUS 정보 검색 플랫폼

Organic and Biomolecular Chemistry

Volumn 12, Issue 24, 2014, Pages 4051-4060

Sp3 C-H oxidation by remote H-radical shift with oxygen- and nitrogen-radicals: A recent update

(2) Chiba, Shunsuke a Chen, Hui a

a Nanyang Technological University (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN;

C-H BOND OXIDATIONS; RADICAL PRECURSOR;

OXYGEN;

EID: 84901684468 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c4ob00469h Document Type: Review

Times cited : (220)

References (69)

1
- 84885070397
- J. L. Jeffrey R. Sarpong Chem. Sci. 2013 4 4092
- (2013) Chem. Sci. , vol.4 , pp. 4092
- Jeffrey, J.L.¹ Sarpong, R.²

2
- 84865838463
- J. Yamaguchi A. D. Yamaguchi K. Itami Angew. Chem., Int. Ed. 2012 51 8960
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 8960
- Yamaguchi, J.¹ Yamaguchi, A.D.² Itami, K.³

3
- 84864120575
- D. Y.-K. Chen S. W. Youn Chem.-Eur. J. 2012 18 9452
- (2012) Chem.-Eur. J. , vol.18 , pp. 9452
- Chen, D.Y.-K.¹ Youn, S.W.²

4
- 84857325043
- M. C. White Science 2012 335 807
- (2012) Science , vol.335 , pp. 807
- White, M.C.¹

5
- 84870014856
- R. T. Gephart III T. H. Warren Organometallics 2012 31 7728
- (2012) Organometallics , vol.31 , pp. 7728
- Gephart III, R.T.¹ Warren, T.H.²

6
- 84863494370
- J. L. Roizen M. E. Harvey J. Du Bois Acc. Chem. Res. 2012 45 911
- (2012) Acc. Chem. Res. , vol.45 , pp. 911
- Roizen, J.L.¹ Harvey, M.E.² Du Bois, J.³

7
- 79959795014
- H. M. L. Davies J. Du Bois J.-Q. Yu Chem. Soc. Rev. 2011 40 1855
- (2011) Chem. Soc. Rev. , vol.40 , pp. 1855
- Davies, H.M.L.¹ Du Bois, J.² Yu, J.-Q.³

8
- 79953249140
- T. Newhouse P. S. Baran Angew. Chem., Int. Ed. 2011 50 3362
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 3362
- Newhouse, T.¹ Baran, P.S.²

9
- 79960488436
- J. Du Bois Org. Process Res. Dev. 2011 15 758
- (2011) Org. Process Res. Dev. , vol.15 , pp. 758
- Du Bois, J.¹

10
- 79961145489
- F. Collet C. Lescot P. Dauban Chem. Soc. Rev. 2011 40 1926
- (2011) Chem. Soc. Rev. , vol.40 , pp. 1926
- Collet, F.¹ Lescot, C.² Dauban, P.³

11
- 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

12
- 69249129394
- F. Collet R. H. Dodd P. Dauban Chem. Commun. 2009 5061
- (2009) Chem. Commun. , pp. 5061
- Collet, F.¹ Dodd, R.H.² Dauban, P.³

13
- 51049091002
- 3 C-H functionalization with C-radicals, see
- M. M. Díaz-Requejo P. J. Pérez Chem. Rev. 2008 108 3379
- (2008) Chem. Rev. , vol.108 , pp. 3379
- Díaz-Requejo, M.M.¹ Pérez, P.J.²

14
- 54149113140
- F. Dénès F. Beaufils P. Renaud Synlett 2008 2389
- (2008) Synlett , pp. 2389
- Dénès, F.¹ Beaufils, F.² Renaud, P.³

15
- 57249084541
- Baran recently used the 2-triazenyl-tosyl moiety installed on aliphatic alcohols and amines for their site-selective desaturation via remote H-radical shift, see
- J. Robertson J. Pillai R. K. Lush Chem. Soc. Rev. 2001 30 94
- (2001) Chem. Soc. Rev. , vol.30 , pp. 94
- Robertson, J.¹ Pillai, J.² Lush, R.K.³

16
- 84864339873
- For reviews, see
- A.-F. Voica A. Mendoza W. R. Gutekunst J. O. Fraga P. S. Baran Nat. Chem. 2012 4 629
- (2012) Nat. Chem. , vol.4 , pp. 629
- Voica, A.-F.¹ Mendoza, A.² Gutekunst, W.R.³ Fraga, J.O.⁴ Baran, P.S.⁵

17
- 84882994233
- Ž. Čeković Tetrahedron 2003 59 8090
- (2003) Tetrahedron , vol.59 , pp. 8090
- Čeković, Z.¹

18
- 0029036335
- For computational and kinetic studies of 1,5-H-radical shift with alkoxy radicals, see
- G. Majetich K. Wheless Tetrahedron 1995 51 7095
- (1995) Tetrahedron , vol.51 , pp. 7095
- Majetich, G.¹ Wheless, K.²

19
- 0000206311
- J. H. Horner S.-H. Choi M. Newcomb Org. Lett. 2000 2 3369
- (2000) Org. Lett. , vol.2 , pp. 3369
- Horner, J.H.¹ Choi, S.-H.² Newcomb, M.³

20
- 0000391922
- For recent selected examples, see
- A. E. Dorigo M. A. McCarrick R. J. Loncharich K. N. Houk J. Am. Chem. Soc. 1990 112 7508
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 7508
- Dorigo, A.E.¹ McCarrick, M.A.² Loncharich, R.J.³ Houk, K.N.⁴

21
- 84866103228
- S. Guyenne E. I. León A. Martín I. Pérez- Martín E. Suárez J. Org. Chem. 2012 77 7371
- (2012) J. Org. Chem. , vol.77 , pp. 7371
- Guyenne, S.¹ León, E.I.² Martín, A.³ Pérez-Martín, I.⁴ Suárez, E.⁵

22
- 56349109448
- C. G. Francisco A. J. Herrera A. R. Kennedy A. Martín D. Melián I. Pérez-Martín L. M. Quintanal E. Suárez Chem.-Eur. J. 2008 14 10369
- (2008) Chem.-Eur. J. , vol.14 , pp. 10369
- Francisco, C.G.¹ Herrera, A.J.² Kennedy, A.R.³ Martín, A.⁴ Melián, D.⁵ Pérez-Martín, I.⁶ Quintanal, L.M.⁷ Suárez, E.⁸

23
- 34447625580
- C. G. Francisco R. Freire A. J. Herrera I. Pérez-Martín E. Suárez Tetrahedron 2007 63 8910
- (2007) Tetrahedron , vol.63 , pp. 8910
- Francisco, C.G.¹ Freire, R.² Herrera, A.J.³ Pérez-Martín, I.⁴ Suárez, E.⁵

24
- 33644652147
- A. Boto D. Hernández R. Hernández E. Suárez J. Org. Chem. 2006 71 1938
- (2006) J. Org. Chem. , vol.71 , pp. 1938
- Boto, A.¹ Hernández, D.² Hernández, R.³ Suárez, E.⁴

25
- 7044239532
- A. Boto D. Hernández R. Hernández E. Suárez Org. Lett. 2004 6 3785
- (2004) Org. Lett. , vol.6 , pp. 3785
- Boto, A.¹ Hernández, D.² Hernández, R.³ Suárez, E.⁴

26
- 0141629765
- J. S. Lee P. L. Fuchs Org. Lett. 2003 5 2247
- (2003) Org. Lett. , vol.5 , pp. 2247
- Lee, J.S.¹ Fuchs, P.L.²

27
- 0037129408
- For a review, see
- C. Betancor R. Freire I. Pérez-Martín T. Prangé E. Suárez Org. Lett. 2002 4 1295
- (2002) Org. Lett. , vol.4 , pp. 1295
- Betancor, C.¹ Freire, R.² Pérez-Martín, I.³ Prangé, T.⁴ Suárez, E.⁵

28
- 42549140767
- N. Hoffmann Chem. Rev. 2008 108 1052
- (2008) Chem. Rev. , vol.108 , pp. 1052
- Hoffmann, N.¹

29
- 0001285236
- Ž. Ĉeković M. Ĉvetković Tetrahedron Lett. 1982 23 3791
- (1982) Tetrahedron Lett. , vol.23 , pp. 3791
- Ĉeković, Z.¹ Ĉvetković, M.²

30
- 49249150332
- Ž. Ĉeković L. Dimitrijević G. Djokić T. Srnić Tetrahedron 1979 35 2021
- (1979) Tetrahedron , vol.35 , pp. 2021
- Ĉeković, Z.¹ Dimitrijević, L.² Djokić, G.³ Srnić, T.⁴

31
- 0001603938
- Ž. Ĉeković M. M. Green J. Am. Chem. Soc. 1974 96 3000
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 3000
- Ĉeković, Z.¹ Green, M.M.²

32
- 77953010333
- R. Kundu Z. T. Ball Org. Lett. 2010 12 2460
- (2010) Org. Lett. , vol.12 , pp. 2460
- Kundu, R.¹ Ball, Z.T.²

33
- 84879977534
- For reviews, see
- P. C. Too Y. L. Tnay S. Chiba Beilstein J. Org. Chem. 2013 9 1217
- (2013) Beilstein J. Org. Chem. , vol.9 , pp. 1217
- Too, P.C.¹ Tnay, Y.L.² Chiba, S.³

34
- 35148843206
- F. Recupero C. Punta Chem. Rev. 2007 107 3800
- (2007) Chem. Rev. , vol.107 , pp. 3800
- Recupero, F.¹ Punta, C.²

35
- 84871696194
- E. Roduner W. Kaim B. Sarjar V. B. Urlacher J. Pleiss R. Gläser W.-D. Einicke G. A. Sprenger U. Beifuß E. Klemm C. Liebner H. Hieronymus S.-F. Hsu B. Plietker S. Laschar ChemCatChem 2013 5 82
- (2013) ChemCatChem , vol.5 , pp. 82
- Roduner, E.¹ Kaim, W.² Sarjar, B.³ Urlacher, V.B.⁴ Pleiss, J.⁵ Gläser, R.⁶ Einicke, W.-D.⁷ Sprenger, G.A.⁸ Beifuß, U.⁹ Klemm, E.¹⁰ Liebner, C.¹¹ Hieronymus, H.¹² Hsu, S.-F.¹³ Plietker, B.¹⁴ Laschar, S.¹⁵

36
- 0000434277
- Y. Ishii S. Sakaguchi T. Iwahama Adv. Synth. Catal. 2001 343 393
- (2001) Adv. Synth. Catal. , vol.343 , pp. 393
- Ishii, Y.¹ Sakaguchi, S.² Iwahama, T.³

37
- 84897586652
- T. Hashimoto D. Hirose T. Taniguchi Angew. Chem., Int. Ed. 2014 53 2730
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 2730
- Hashimoto, T.¹ Hirose, D.² Taniguchi, T.³

38
- 84891445593
- A. M. Adams J. Du Bois Chem. Sci. 2014 5 656
- (2014) Chem. Sci. , vol.5 , pp. 656
- Adams, A.M.¹ Du Bois, J.²

39
- 70349782189
- N. D. Litvinas B. H. Brodsky J. Du Bois Angew. Chem., Int. Ed. 2009 48 4513
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 4513
- Litvinas, N.D.¹ Brodsky, B.H.² Du Bois, J.³

40
- 27644563193
- B. H. Brodsky J. Du Bois J. Am. Chem. Soc. 2005 127 15391
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 15391
- Brodsky, B.H.¹ Du Bois, J.²

41
- 69849109789
- C. P. Allen T. Benkovics A. K. Turek T. P. Yoon J. Am. Chem. Soc. 2009 131 12560
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 12560
- Allen, C.P.¹ Benkovics, T.² Turek, A.K.³ Yoon, T.P.⁴

42
- 84874234410
- The same group reported that the reactions in the presence of water afforded 4-hydroxy-5-nitropenthyl nitrate, see
- T. Taniguchi Y. Sugiura T. Hatta A. Yajima H. Ishibashi Chem. Commun. 2013 49 2198
- (2013) Chem. Commun. , vol.49 , pp. 2198
- Taniguchi, T.¹ Sugiura, Y.² Hatta, T.³ Yajima, A.⁴ Ishibashi, H.⁵

43
- 84885066869
- D. Hirose T. Taniguchi Beilstein J. Org. Chem. 2013 9 1713
- (2013) Beilstein J. Org. Chem. , vol.9 , pp. 1713
- Hirose, D.¹ Taniguchi, T.²

44
- 38149026950
- S.-S. Chong Y. Fu L. Liu Q.-X. Guo J. Phys. Chem. A 2007 111 13112
- (2007) J. Phys. Chem. A , vol.111 , pp. 13112
- Chong, S.-S.¹ Fu, Y.² Liu, L.³ Guo, Q.-X.⁴

45
- 4344561879
- Han reported the addition of iminoxyl radicals onto intramolecular alkenes, see
- D. A. Pratt J. A. Blake P. Mulder J. C. Walton H.-G. Korth K. U. Ingold J. Am. Chem. Soc. 2004 126 10667
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 10667
- Pratt, D.A.¹ Blake, J.A.² Mulder, P.³ Walton, J.C.⁴ Korth, H.-G.⁵ Ingold, K.U.⁶

46
- 84865437035
- B. Han X.-L. Yang R. Fang W. Yu C. Wang X.-Y. Duan S. Liu Angew. Chem., Int. Ed. 2012 51 8816
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 8816
- Han, B.¹ Yang, X.-L.² Fang, R.³ Yu, W.⁴ Wang, C.⁵ Duan, X.-Y.⁶ Liu, S.⁷

47
- 84880028139
- X. Zhu Y.-F. Wang W. Ren F.-L. Zhang S. Chiba Org. Lett. 2013 15 3214
- (2013) Org. Lett. , vol.15 , pp. 3214
- Zhu, X.¹ Wang, Y.-F.² Ren, W.³ Zhang, F.-L.⁴ Chiba, S.⁵

48
- 84882966055
- F.-L. Zhang Y.-F. Wang S. Chiba Org. Biomol. Chem. 2013 11 6003
- (2013) Org. Biomol. Chem. , vol.11 , pp. 6003
- Zhang, F.-L.¹ Wang, Y.-F.² Chiba, S.³

49
- 33748839705
- S. L. Titouania J.-P. Lavergne P. Viallefonta E. Jacquierb Tetrahedron 1980 36 2961
- (1980) Tetrahedron , vol.36 , pp. 2961
- Titouania, S.L.¹ Lavergne, J.-P.² Viallefonta, P.³ Jacquierb, E.⁴

50
- 33947471447
- E. J. Corey W. R. Hertler J. Am. Chem. Soc. 1960 82 1657
- (1960) J. Am. Chem. Soc. , vol.82 , pp. 1657
- Corey, E.J.¹ Hertler, W.R.²

51
- 84979191568
- K. Löffler C. Freytag Ber. 1909 42 3427
- (1909) Ber. , vol.42 , pp. 3427
- Löffler, K.¹ Freytag, C.²

52
- 84978590581
- A. W. Hofmann Ber. 1883 16 558
- (1883) Ber. , vol.16 , pp. 558
- Hofmann, A.W.¹

53
- 33746108032
- 2 conditions, see
- L. R. Reddy B. V. S. Reddy E. J. Corey Org. Lett. 2006 8 2819
- (2006) Org. Lett. , vol.8 , pp. 2819
- Reddy, L.R.¹ Reddy, B.V.S.² Corey, E.J.³

54
- 35948974648
- R. Fan D. Pu F. Wen J. Wu J. Org. Chem. 2007 72 8994
- (2007) J. Org. Chem. , vol.72 , pp. 8994
- Fan, R.¹ Pu, D.² Wen, F.³ Wu, J.⁴

55
- 44949086718
- K. Chen J. M. Richter P. S. Baran J. Am. Chem. Soc. 2008 130 7247
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 7247
- Chen, K.¹ Richter, J.M.² Baran, P.S.³

56
- 67349149964
- K. Chen P. S. Baran Nature 2009 459 824
- (2009) Nature , vol.459 , pp. 824
- Chen, K.¹ Baran, P.S.²

57
- 84865276096
- For a review, see
- H. F. Motiwala B. Gülgeze J. Aubé J. Org. Chem. 2012 77 7005
- (2012) J. Org. Chem. , vol.77 , pp. 7005
- Motiwala, H.F.¹ Gülgeze, B.² Aubé, J.³

58
- 84891572017
- in, ed. S. Bräse and K. Banert, Wiley, p. 239 Kim reported 1,5-H radical shift of N-tributyltin substituted aminyl radicals, see
- C. Jimeno and P. Renaud, in Organic Azides: Syntheses and Applications, ed., S. Bräse, and, K. Banert, Wiley, 2010, p. 239
- (2010) Organic Azides: Syntheses and Applications
- Jimeno, C.¹ Renaud, P.²

59
- 0030908396
- S. Kim K. M. Yeon K. S. Yoon Tetrahedron Lett. 1997 38 3919
- (1997) Tetrahedron Lett. , vol.38 , pp. 3919
- Kim, S.¹ Yeon, K.M.² Yoon, K.S.³

60
- 78650429673
- H. Lu H. jiang L. Wojtas X. P. Zhang Angew. Chem., Int. Ed. 2010 49 10192
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 10192
- Lu, H.¹ Jiang, H.² Wojtas, L.³ Zhang, X.P.⁴

61
- 84877354471
- Katsuki reported enantioselective intramolecular benzylic C-H amination with sulfonyl azides catalyzed by Ir(iii)-salen complexes, see
- E. T. Hennessy T. A. Betley Science 2013 340 591
- (2013) Science , vol.340 , pp. 591
- Hennessy, E.T.¹ Betley, T.A.²

62
- 80053904157
- For a personal account, see
- M. Ichinose H. Suematsu Y. Yasuromi Y. Nishioka T. Uchida T. Katsuki Angew. Chem., Int. Ed. 2011 50 9884
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 9884
- Ichinose, M.¹ Suematsu, H.² Yasuromi, Y.³ Nishioka, Y.⁴ Uchida, T.⁵ Katsuki, T.⁶

63
- 84890608542
- S. Chiba Bull. Chem. Soc. Jpn. 2013 86 1400
- (2013) Bull. Chem. Soc. Jpn. , vol.86 , pp. 1400
- Chiba, S.¹

64
- 84875876384
- P. Zhu B. M. T. Tong R. Wang K. J. Chen S. Foo H. C. Chong X. L. Wang G. Y. Ang S. Chiba N. S. Tan Cell Death Dis. 2013 4 e552
- (2013) Cell Death Dis. , vol.4 , pp. 552
- Zhu, P.¹ Tong, B.M.T.² Wang, R.³ Chen, K.J.⁴ Foo, S.⁵ Chong, H.C.⁶ Wang, X.L.⁷ Ang, G.Y.⁸ Chiba, S.⁹ Tan, N.S.¹⁰

65
- 79953214612
- L. Zhang G. Y. Ang S. Chiba Org. Lett. 2011 13 1622
- (2011) Org. Lett. , vol.13 , pp. 1622
- Zhang, L.¹ Ang, G.Y.² Chiba, S.³

66
- 84864189378
- Y.-F. Wang H. Chen X. Zhu S. Chiba J. Am. Chem. Soc. 2012 134 11980
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 11980
- Wang, Y.-F.¹ Chen, H.² Zhu, X.³ Chiba, S.⁴

67
- 84874084114
- H. Chen S. Chiba Org. Lett. 2013 15 212
- (2013) Org. Lett. , vol.15 , pp. 212
- Chen, H.¹ Chiba, S.²

68
- 84888987400
- Han reported the addition of hydrazone radicals onto intramolecular alkenes, see
- H. Chen S. Chiba Org. Biomol. Chem. 2014 12 42
- (2014) Org. Biomol. Chem. , vol.12 , pp. 42
- Chen, H.¹ Chiba, S.²

69
- 84887087987
- X.-Y. Duan X.-L. Yang R. Fang X.-X. Peng W. Yu B. Han J. Org. Chem. 2013 78 10692
- (2013) J. Org. Chem. , vol.78 , pp. 10692
- Duan, X.-Y.¹ Yang, X.-L.² Fang, R.³ Peng, X.-X.⁴ Yu, W.⁵ Han, B.⁶

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