SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 53, Issue 10, 2014, Pages 2730-2734

Direct synthesis of 1,4-diols from alkenes by iron-catalyzed aerobic hydration and C-H hydroxylation

(3) Hashimoto, Takuma a Hirose, Daisuke a Taniguchi, Tsuyoshi a

a KANAZAWA UNIVERSITY (Japan)

Author keywords

C H oxygenation; iron catalysis; oxygen; radical reactions; synthetic methods

Indexed keywords

DIRECT SYNTHESIS; HYDROGEN SHIFTS; IRON CATALYSIS; IRON PHTHALOCYANINES; RADICAL REACTIONS; REACTION SYSTEM; SODIUM BORO HYDRIDES; SYNTHETIC METHODS;

CATALYSIS; HYDRATION; HYDROCARBONS; HYDROGEN; HYDROXYLATION; IRON; OXYGEN; OXYGENATION; REACTION KINETICS;

IRON COMPOUNDS;

ALCOHOL DERIVATIVE; ALKENE; IRON; OXYGEN;

ARTICLE; C H OXYGENATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; IRON CATALYSIS; RADICAL REACTIONS; SYNTHESIS; SYNTHETIC METHODS;

C H OXYGENATION; IRON CATALYSIS; OXYGEN; RADICAL REACTIONS; SYNTHETIC METHODS;

ALCOHOLS; ALKENES; CATALYSIS; HYDROXYLATION; IRON; MOLECULAR STRUCTURE;

EID: 84897586652 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201308675 Document Type: Article

Times cited : (71)

References (76)

1
- 0003412412
- Wiley, New York
- M. B. Smith, J. March, March's Advanced Organic Chemistry, 5th ed., Wiley, New York, 2001
- (2001) March's Advanced Organic Chemistry, 5th Ed.
- Smith, M.B.¹ March, J.²

2
- 0003928002
- Elsevier, Amsterdam
- Comprehensive Organic Functional Group Transformations II, Vol. 2, (Eds.:, A. R. Katrinsky, R. J. K. Taylor,), Elsevier, Amsterdam, 2005.
- (2005) Comprehensive Organic Functional Group Transformations II , vol.2
- Katrinsky, A.R.¹ Taylor, R.J.K.²

3
- 80052918192
- G. Dong, P. Teo, Z. K. Wickens, R. H. Grubbs, Science 2011, 333, 1609-1612
- (2011) Science , vol.333 , pp. 1609-1612
- Dong, G.¹ Teo, P.² Wickens, Z.K.³ Grubbs, R.H.⁴

4
- 84867783056
- L. Li, S. B. Herzon, J. Am. Chem. Soc. 2012, 134, 17376-17379.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 17376-17379
- Li, L.¹ Herzon, S.B.²

5
- 79957724198
- K. Takahashi, M. Yamashita, T. Ichihara, K. Nakano, K. Nozaki, Angew. Chem. 2010, 122, 4590-4592
- (2010) Angew. Chem. , vol.122 , pp. 4590-4592
- Takahashi, K.¹ Yamashita, M.² Ichihara, T.³ Nakano, K.⁴ Nozaki, K.⁵

6
- 77953655221
- Angew. Chem. Int. Ed. 2010, 49, 4488-4490.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 4488-4490

7
- 80051582856
- P. E. Gormisky, M. C. White, J. Am. Chem. Soc. 2011, 133, 12584-12589
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 12584-12589
- Gormisky, P.E.¹ White, M.C.²

8
- 84897601655
- D. Huang, H. Wang, F. Xue, Y. Shi, Org. Lett. 2011, 13, 7269-7274
- (2011) Org. Lett. , vol.13 , pp. 7269-7274
- Huang, D.¹ Wang, H.² Xue, F.³ Shi, Y.⁴

9
- 84882253796
- I. I. Strambeanu, M. C. White, J. Am. Chem. Soc. 2013, 135, 12032-12037.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 12032-12037
- Strambeanu, I.I.¹ White, M.C.²

10
- 84891568337
- Wiley-VCH, Weinheim.
- Modern Oxidation Methods, 2nd ed. (Ed.:, J.-E. Bäckvall,), Wiley-VCH, Weinheim, 2010.
- (2010) Modern Oxidation Methods, 2nd Ed.
- Bäckvall, J.-E.¹

11
- 80052436882
- Y. Feng, J. England, L. Que, Jr., ACS Catal. 2011, 1, 1035-1042
- (2011) ACS Catal. , vol.1 , pp. 1035-1042
- Feng, Y.¹ England, J.² Que Jr., L.³

12
- 84875822107
- M. J. Rawling, N. C. O. Tomkinson, Org. Biomol. Chem. 2013, 11, 1434-1440.
- (2013) Org. Biomol. Chem. , vol.11 , pp. 1434-1440
- Rawling, M.J.¹ Tomkinson, N.C.O.²

13
- 33644531590
- S. E. Bode, M. Wolberg, M. Müller, Synthesis 2006, 557-588
- (2006) Synthesis , pp. 557-588
- Bode, S.E.¹ Wolberg, M.² Müller, M.³

14
- 58149173869
- C. Oger, Y. Brinkmann, S. Bouazzaoui, T. Durand, J.-M. Galano, Org. Lett. 2008, 10, 5087-5090
- (2008) Org. Lett. , vol.10 , pp. 5087-5090
- Oger, C.¹ Brinkmann, Y.² Bouazzaoui, S.³ Durand, T.⁴ Galano, J.-M.⁵

15
- 78651400965
- A. Robinson, V. K. Aggarwal, Angew. Chem. 2010, 122, 6823-6825
- (2010) Angew. Chem. , vol.122 , pp. 6823-6825
- Robinson, A.¹ Aggarwal, V.K.²

16
- 77956510772
- Angew. Chem. Int. Ed. 2010, 49, 6673-6675.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 6673-6675

17
- 44949086718
- K. Chen, J. M. Richter, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 7247-7249
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 7247-7249
- Chen, K.¹ Richter, J.M.² Baran, P.S.³

18
- 78651477797
- Y. Jiao, C. Cao, Z. Zhou, Org. Lett. 2011, 13, 180-183
- (2011) Org. Lett. , vol.13 , pp. 180-183
- Jiao, Y.¹ Cao, C.² Zhou, Z.³

19
- 80054751613
- H. Y. Cho, Z. Yu, J. P. Morken, Org. Lett. 2011, 13, 5267-5269
- (2011) Org. Lett. , vol.13 , pp. 5267-5269
- Cho, H.Y.¹ Yu, Z.² Morken, J.P.³

20
- 84856915007
- P. A. Evans, A. Grisin, M. J. Lawler, J. Am. Chem. Soc. 2012, 134, 2856-2859.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 2856-2859
- Evans, P.A.¹ Grisin, A.² Lawler, M.J.³

21
- 0242660163
- R. Ballini, L. Barboni, G. Giarlo, J. Org. Chem. 2003, 68, 9173-9176
- (2003) J. Org. Chem. , vol.68 , pp. 9173-9176
- Ballini, R.¹ Barboni, L.² Giarlo, G.³

22
- 79955640904
- R. F. de La Pradilla, I. Colomer, M. Ureña, A. Viso, Org. Lett. 2011, 13, 2468-2471
- (2011) Org. Lett. , vol.13 , pp. 2468-2471
- De La Pradilla, R.F.¹ Colomer, I.² Ureña, M.³ Viso, A.⁴

23
- 83455172514
- M. Tortosa, Angew. Chem. 2011, 123, 4036-4039
- (2011) Angew. Chem. , vol.123 , pp. 4036-4039
- Tortosa, M.¹

24
- 79954582746
- Angew. Chem. Int. Ed. 2011, 50, 3950-3953
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 3950-3953

25
- 84857217982
- A. Robinson, V. K. Aggarwal, Org. Biomol. Chem. 2012, 10, 1795-1801.
- (2012) Org. Biomol. Chem. , vol.10 , pp. 1795-1801
- Robinson, A.¹ Aggarwal, V.K.²

26
- 67649964459
- H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 9134-9135
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 9134-9135
- Burks, H.E.¹ Kliman, L.T.² Morken, J.P.³

27
- 77957164462
- R. J. Ely, J. P. Morken, Org. Lett. 2010, 12, 4348-4351
- (2010) Org. Lett. , vol.12 , pp. 4348-4351
- Ely, R.J.¹ Morken, J.P.²

28
- 84879977534
- P. C. Too, Y. L. Tnay, S. Chiba, Beilstein J. Org. Chem. 2013, 9, 1217-1225.
- (2013) Beilstein J. Org. Chem. , vol.9 , pp. 1217-1225
- Too, P.C.¹ Tnay, Y.L.² Chiba, S.³

29
- 33645674829
- K. Godula, D. Sames, Science 2006, 312, 67-72
- (2006) Science , vol.312 , pp. 67-72
- Godula, K.¹ Sames, D.²

30
- 84874247192
- P. S. Baran, Y. Ishihara, Synlett 2010, 1733-1745
- (2010) Synlett , pp. 1733-1745
- Baran, P.S.¹ Ishihara, Y.²

31
- 77349091080
- P. R. Ortiz de Montellano, Chem. Rev. 2010, 110, 932-948
- (2010) Chem. Rev. , vol.110 , pp. 932-948
- Ortiz De Montellano, P.R.¹

32
- 79960929540
- T. Newhouse, P. S. Baran, Angew. Chem. 2011, 123, 3422-3435
- (2011) Angew. Chem. , vol.123 , pp. 3422-3435
- Newhouse, T.¹ Baran, P.S.²

33
- 79953249140
- Angew. Chem. Int. Ed. 2011, 50, 3362-3374
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 3362-3374

34
- 79961143500
- M. Zhou, R. H. Crabtree, Chem. Soc. Rev. 2011, 40, 1875-1884
- (2011) Chem. Soc. Rev. , vol.40 , pp. 1875-1884
- Zhou, M.¹ Crabtree, R.H.²

35
- 79959790191
- C.-M. Che, V. K.-Y. Lo, C.-Y. Zhou, J.-S. Huang, Chem. Soc. Rev. 2011, 40, 1950-1975
- (2011) Chem. Soc. Rev. , vol.40 , pp. 1950-1975
- Che, C.-M.¹ Lo, V.K.-Y.² Zhou, C.-Y.³ Huang, J.-S.⁴

36
- 84857325043
- M. C. White, Science 2012, 335, 807-809.
- (2012) Science , vol.335 , pp. 807-809
- White, M.C.¹

37
- 77955804261
- E. McNeill, J. Du Bois, J. Am. Chem. Soc. 2010, 132, 10202-10204
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 10202-10204
- McNeill, E.¹ Du Bois, J.²

38
- 77952806509
- K. Kamata, K. Yonehara, Y. Nakagawa, K. Uehara, N. Mizuno, Nat. Chem. 2010, 2, 478-483
- (2010) Nat. Chem. , vol.2 , pp. 478-483
- Kamata, K.¹ Yonehara, K.² Nakagawa, Y.³ Uehara, K.⁴ Mizuno, N.⁵

39
- 84862186271
- M. A. Bigi, S. A. Reed, M. C. White, J. Am. Chem. Soc. 2012, 134, 9721-9726
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 9721-9726
- Bigi, M.A.¹ Reed, S.A.² White, M.C.³

40
- 84867553616
- Z. Ren, F. Mo, G. Dong, J. Am. Chem. Soc. 2012, 134, 16991-16994
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 16991-16994
- Ren, Z.¹ Mo, F.² Dong, G.³

41
- 84857754603
- E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70-73
- (2012) Nature , vol.483 , pp. 70-73
- Simmons, E.M.¹ Hartwig, J.F.²

42
- 84864199567
- E. McNeill, J. Du Bois, Chem. Sci. 2012, 3, 1810-1813
- (2012) Chem. Sci. , vol.3 , pp. 1810-1813
- McNeill, E.¹ Du Bois, J.²

43
- 84860797573
- S.-Y. Zhang, G. He, Y. Zhao, K. Wright, W. A. Nack, G. Chen, J. Am. Chem. Soc. 2012, 134, 7313-7316
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 7313-7316
- Zhang, S.-Y.¹ He, G.² Zhao, Y.³ Wright, K.⁴ Nack, W.A.⁵ Chen, G.⁶

44
- 84873960171
- L. Gõmez, M. Canta, D. Font, I. Prat, X. Ribas, M. Costas, J. Org. Chem. 2013, 78, 1421-1433
- (2013) J. Org. Chem. , vol.78 , pp. 1421-1433
- Gõmez, L.¹ Canta, M.² Font, D.³ Prat, I.⁴ Ribas, X.⁵ Costas, M.⁶

45
- 84892165305
- S. A. Moteki, A. Usui, T. Zhang, C. R. Solorio Alvarado, K. Maruoka, Angew. Chem. 2013, 125, 8819-8822
- (2013) Angew. Chem. , vol.125 , pp. 8819-8822
- Moteki, S.A.¹ Usui, A.² Zhang, T.³ Solorio Alvarado, C.R.⁴ Maruoka, K.⁵

46
- 84882437681
- Angew. Chem. Int. Ed. 2013, 52, 8657-8660
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 8657-8660

47
- 84884871427
- P. E. Gormisky, M. C. White, J. Am. Chem. Soc. 2013, 135, 14052-14055.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 14052-14055
- Gormisky, P.E.¹ White, M.C.²

48
- 0141570904
- Ž. Čekovic̈, Tetrahedron 2003, 59, 8073-8090; for recent examples, see
- (2003) Tetrahedron , vol.59 , pp. 8073-8090
- Čekovic̈, Z.¹

49
- 77953010333
- R. Kundu, Z. T. Ball, Org. Lett. 2010, 12, 2460-2463
- (2010) Org. Lett. , vol.12 , pp. 2460-2463
- Kundu, R.¹ Ball, Z.T.²

50
- 84864339873
- A.-F. Voica, A. Mendoza, W. R. Gutekunst, J. O. Fraga, P. S. Baran, Nat. Chem. 2012, 4, 629-635
- (2012) Nat. Chem. , vol.4 , pp. 629-635
- Voica, A.-F.¹ Mendoza, A.² Gutekunst, W.R.³ Fraga, J.O.⁴ Baran, P.S.⁵

51
- 84880028139
- X. Zhu, Y.-F. Wang, W. Ren, F.-L. Zhang, S. Chiba, Org. Lett. 2013, 15, 3214-3217
- (2013) Org. Lett. , vol.15 , pp. 3214-3217
- Zhu, X.¹ Wang, Y.-F.² Ren, W.³ Zhang, F.-L.⁴ Chiba, S.⁵

52
- 84877354471
- E. T. Hennessy, T. A. Betley, Science 2013, 340, 591-595
- (2013) Science , vol.340 , pp. 591-595
- Hennessy, E.T.¹ Betley, T.A.²

53
- 84874234410
- T. Taniguchi, Y. Sugiura, T. Hatta, A. Yajima, H. Ishibashi, Chem. Commun. 2013, 49, 2198-2200
- (2013) Chem. Commun. , vol.49 , pp. 2198-2200
- Taniguchi, T.¹ Sugiura, Y.² Hatta, T.³ Yajima, A.⁴ Ishibashi, H.⁵

54
- 84885066869
- see also Ref. [10c] and references therein.
- D. Hirose, T. Taniguchi, Beilstein J. Org. Chem. 2013, 9, 1713-1717; see also Ref. [10c] and references therein.
- (2013) Beilstein J. Org. Chem. , vol.9 , pp. 1713-1717
- Hirose, D.¹ Taniguchi, T.²

55
- 33845471665
- T. Okamoto, S. Oka, J. Org. Chem. 1984, 49, 1589-1594
- (1984) J. Org. Chem. , vol.49 , pp. 1589-1594
- Okamoto, T.¹ Oka, S.²

56
- 0037567608
- T. Sugimori, S.-i. Horike, S. Tsumura, M. Handa, K. Kasuga, Inorg. Chim. Acta 1998, 283, 275-278
- (1998) Inorg. Chim. Acta , vol.283 , pp. 275-278
- Sugimori, T.¹ Horike, S.-I.² Tsumura, S.³ Handa, M.⁴ Kasuga, K.⁵

57
- 63849248540
- S. Prateeptongkum, I. Jovel, R. Jackstell, N. Vogl, C. Weckbecker, M. Beller, Chem. Commun. 2009, 1990-1992
- (2009) Chem. Commun. , pp. 1990-1992
- Prateeptongkum, S.¹ Jovel, I.² Jackstell, R.³ Vogl, N.⁴ Weckbecker, C.⁵ Beller, M.⁶

58
- 73949140641
- T. Taniguchi, N. Goto, A. Nishibata, H. Ishibashi, Org. Lett. 2010, 12, 112-115; for additions and corrections, see
- (2010) Org. Lett. , vol.12 , pp. 112-115
- Taniguchi, T.¹ Goto, N.² Nishibata, A.³ Ishibashi, H.⁴

59
- 78049520751
- T. Taniguchi, N. Goto, A. Nishibata, H. Ishibashi, Org. Lett. 2010, 12, 5084
- (2010) Org. Lett. , vol.12 , pp. 5084
- Taniguchi, T.¹ Goto, N.² Nishibata, A.³ Ishibashi, H.⁴

60
- 84858665556
- E. K. Leggans, T. J. Barker, K. K. Duncan, D. L. Boger, Org. Lett. 2012, 14, 1428-1431
- (2012) Org. Lett. , vol.14 , pp. 1428-1431
- Leggans, E.K.¹ Barker, T.J.² Duncan, K.K.³ Boger, D.L.⁴

61
- 84865431754
- T. J. Barker, D. L. Boger, J. Am. Chem. Soc. 2012, 134, 13588-13591
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 13588-13591
- Barker, T.J.¹ Boger, D.L.²

62
- 84872381103
- A. Ekomié, G. Lefèvre, L. Fensterbank, E. Lacôte, M. Malacria, C. Ollivier, A. Jutand, Angew. Chem. 2012, 124, 7048-7052
- (2012) Angew. Chem. , vol.124 , pp. 7048-7052
- Ekomié, A.¹ Lefèvre, G.² Fensterbank, L.³ Lacôte, E.⁴ Malacria, M.⁵ Ollivier, C.⁶ Jutand, A.⁷

63
- 84863654017
- Angew. Chem. Int. Ed. 2012, 51, 6942-6946.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 6942-6946

64
- 84885621298
- For a review on metal phthalocyanines, see:, A. B. Sorokin, Chem. Rev. 2013, 113, 8152-8191.
- (2013) Chem. Rev. , vol.113 , pp. 8152-8191
- Sorokin, A.B.¹

65
- 21944440277
- T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329-2364
- (2005) Chem. Rev. , vol.105 , pp. 2329-2364
- Punniyamurthy, T.¹ Velusamy, S.² Iqbal, J.³

66
- 54749090939
- J. Piera, J.-E. Bäckvall, Angew. Chem. 2008, 120, 3558-3576
- (2008) Angew. Chem. , vol.120 , pp. 3558-3576
- Piera, J.¹ Bäckvall, J.-E.²

67
- 44049092112
- Angew. Chem. Int. Ed. 2008, 47, 3506-3523
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3506-3523

68
- 84863434722
- A. N. Campbell, S. S. Stahl, Acc. Chem. Res. 2012, 45, 851-863.
- (2012) Acc. Chem. Res. , vol.45 , pp. 851-863
- Campbell, A.N.¹ Stahl, S.S.²

69
- 33750549800
- W. Nam, M. H. Lim, S.-Y. Oh, J. H. Lee, H. J. Lee, S. K. Woo, C. Kim, W. Shin, Angew. Chem. 2000, 112, 3792-3795
- (2000) Angew. Chem. , vol.112 , pp. 3792-3795
- Nam, W.¹ Lim, M.H.² Oh, S.-Y.³ Lee, J.H.⁴ Lee, H.J.⁵ Woo, S.K.⁶ Kim, C.⁷ Shin, W.⁸

70
- 0034675675
- Angew. Chem. Int. Ed. 2000, 39, 3646-3649
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3646-3649

71
- 0034722232
- W. Nam, M. H. Lim, S.-Y. Oh, Inorg. Chem. 2000, 39, 5572-5575
- (2000) Inorg. Chem. , vol.39 , pp. 5572-5575
- Nam, W.¹ Lim, M.H.² Oh, S.-Y.³

72
- 0037100448
- W. Nam, S. W. Jin, M. H. Lim, J. Y. Ryu, C. Kim, Inorg. Chem. 2002, 41, 3647-3652.
- (2002) Inorg. Chem. , vol.41 , pp. 3647-3652
- Nam, W.¹ Jin, S.W.² Lim, M.H.³ Ryu, J.Y.⁴ Kim, C.⁵

73
- 0041689437
- J. Berkowitz, G. B. Ellison, D. Gutman, J. Phys. Chem. 1994, 98, 2744-2765
- (1994) J. Phys. Chem. , vol.98 , pp. 2744-2765
- Berkowitz, J.¹ Ellison, G.B.² Gutman, D.³

74
- 0037393779
- S. J. Blanksby, G. B. Ellison, Acc. Chem. Res. 2003, 36, 255-263.
- (2003) Acc. Chem. Res. , vol.36 , pp. 255-263
- Blanksby, S.J.¹ Ellison, G.B.²

75
- 4644275807
- B. Meunier, S. P. de Visser, S. Shaik, Chem. Rev. 2004, 104, 3947-3980
- (2004) Chem. Rev. , vol.104 , pp. 3947-3980
- Meunier, B.¹ De Visser, S.P.² Shaik, S.³

76
- 80052135332
- references therein.
- S. Kille, F. E. Zilly, J. P. Acevedo, M. T. Reetz, Nat. Chem. 2011, 3, 738-743, and references therein.
- (2011) Nat. Chem. , vol.3 , pp. 738-743
- Kille, S.¹ Zilly, F.E.² Acevedo, J.P.³ Reetz, M.T.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.