SCOPUS 정보 검색 플랫폼

Volumn 21, Issue 9, 2015, Pages 3815-3820

A metalloenzyme-like catalytic system for the chemoselective oxidative cross-coupling of primary amines to imines under ambient conditions

(2) Largeron, Martine a Fleury, Maurice Bernard a

a UNIVERSITÉ PARIS DESCARTES (France)

Author keywords

Cross coupling; Cycloaddition; Homogeneous catalysis; Oxidation; Primary amines

Indexed keywords

AMINES; CATALYSTS; CATALYTIC OXIDATION; CHEMICAL REACTIONS; CYCLOADDITION; MOLECULAR OXYGEN; OXIDATION; REACTION KINETICS;

AMBIENT CONDITIONS; COOPERATIVE CATALYTIC SYSTEMS; COPPER AMINE OXIDASE; CROSS-COUPLINGS; HOMOGENEOUS CATALYSIS; PRIMARY AMINES; SELECTIVE OXIDATION; SYNERGISTIC COMBINATIONS;

NITROGEN COMPOUNDS;

ALDEHYDE; AMINE; COPPER; IMINE; IMINOQUINONE; METALLOPROTEIN; QUINONE DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALDEHYDES; AMINES; CATALYSIS; COPPER; IMINES; METALLOPROTEINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; QUINONES;

EID: 84923052775 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201405843 Document Type: Article

Times cited : (49)

References (67)

1
- 84884645708
- a) R. D. Patil, S. Adimurthy, Asian J. Org. Chem. 2013, 2, 726-744;
- (2013) Asian J. Org. Chem. , vol.2 , pp. 726-744
- Patil, R.D.¹ Adimurthy, S.²

2
- 84872589106
- b) R. J. Angelici, Catal. Sci. Technol. 2013, 3, 279-296;
- (2013) Catal. Sci. Technol. , vol.3 , pp. 279-296
- Angelici, R.J.¹

3
- 84886624569
- c) W. Qin, S. Long, M. Panunzio, S. Biondi, Molecules 2013, 18, 12264-12289;
- (2013) Molecules , vol.18 , pp. 12264-12289
- Qin, W.¹ Long, S.² Panunzio, M.³ Biondi, S.⁴

4
- 84915732883
- d) B. L. Ryland, S. S. Stahl, Angew. Chem. 2014, 126, 8968-8983;
- (2014) Angew. Chem. , vol.126 , pp. 8968-8983
- Ryland, B.L.¹ Stahl, S.S.²

5
- 84906069534
- Angew. Chem. Int. Ed. 2014, 53, 8824-8838.
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 8824-8838

6
- 84870904217
- a) J. F. Soulé, H. Miyamura, S. Kobayashi, Chem. Commun. 2013, 49, 355-357;
- (2013) Chem. Commun. , vol.49 , pp. 355-357
- Soulé, J.F.¹ Miyamura, H.² Kobayashi, S.³

7
- 84901625690
- b) B. Chen, J. Li, W. Dai, L. Wang, S. Gao, Green Chem. 2014, 16, 3328-3334;
- (2014) Green Chem. , vol.16 , pp. 3328-3334
- Chen, B.¹ Li, J.² Dai, W.³ Wang, L.⁴ Gao, S.⁵

8
- 84903731605
- c) L. Han, P. Xing, B. Jiang, Org. Lett. 2014, 16, 3428-3431;
- (2014) Org. Lett. , vol.16 , pp. 3428-3431
- Han, L.¹ Xing, P.² Jiang, B.³

9
- 84908009944
- d) M. Guan, C. Wang, J. Zhang, Y. Zhao, RSC Adv. 2014, 4, 48777-48782;
- (2014) RSC Adv. , vol.4 , pp. 48777-48782
- Guan, M.¹ Wang, C.² Zhang, J.³ Zhao, Y.⁴

10
- 84920843636
- e) M. Tamura, K. Tomishige, Angew. Chem. Int. Ed. 2015, 54, 864-867;
- (2015) Angew. Chem. Int. Ed. , vol.54 , pp. 864-867
- Tamura, M.¹ Tomishige, K.²

11
- 84922997207
- Angew. Chem. 2015, 127, 878-881.
- (2015) Angew. Chem. , vol.127 , pp. 878-881

12
- 17444428137
- a) J. S. M. Samec, A. H. Ell, J. E. Bäckvall, Chem. Eur. J. 2005, 11, 2327-2334;
- (2005) Chem. Eur. J. , vol.11 , pp. 2327-2334
- Samec, J.S.M.¹ Ell, A.H.² Bäckvall, J.E.³

13
- 34548280289
- b) B. Zhu, R. J. Angelici, Chem. Commun. 2007, 2157-2159;
- (2007) Chem. Commun. , pp. 2157-2159
- Zhu, B.¹ Angelici, R.J.²

14
- 84892140511
- c) A. E. Wendlandt, S. S. Stahl, J. Am. Chem. Soc. 2014, 136, 506-512;
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 506-512
- Wendlandt, A.E.¹ Stahl, S.S.²

15
- 84906730322
- d) A. E. Wendlandt, S. S. Stahl, J. Am. Chem. Soc. 2014, 136, 11910-11913.
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 11910-11913
- Wendlandt, A.E.¹ Stahl, S.S.²

16
- 84861820939
- M. T. Schümperli, C. Hammond, I. Hermans, ACS Catal. 2012, 2, 1108-1117.
- (2012) ACS Catal. , vol.2 , pp. 1108-1117
- Schümperli, M.T.¹ Hammond, C.² Hermans, I.³

17
- 84884623048
- M. Largeron, Eur. J. Org. Chem. 2013, 5225-5235.
- (2013) Eur. J. Org. Chem. , pp. 5225-5235
- Largeron, M.¹

18
- 79960451437
- a) R. D. Patil, S. Adimurthy, Adv. Synth. Catal. 2011, 353, 1695-1700;
- (2011) Adv. Synth. Catal. , vol.353 , pp. 1695-1700
- Patil, R.D.¹ Adimurthy, S.²

19
- 84857229457
- b) Z. Hu, F. M. Kerton, Org. Biomol. Chem. 2012, 10, 1618-1624;
- (2012) Org. Biomol. Chem. , vol.10 , pp. 1618-1624
- Hu, Z.¹ Kerton, F.M.²

20
- 84864973752
- c) R. D. Patil, S. Adimurthy, RSC Adv. 2012, 2, 5119-5122;
- (2012) RSC Adv. , vol.2 , pp. 5119-5122
- Patil, R.D.¹ Adimurthy, S.²

21
- 84876718293
- d) B. Huang, H. Tian, S. Lin, M. Xie, X. Yu, Q. Xu, Tetrahedron Lett. 2013, 54, 2861-2864;
- (2013) Tetrahedron Lett. , vol.54 , pp. 2861-2864
- Huang, B.¹ Tian, H.² Lin, S.³ Xie, M.⁴ Yu, X.⁵ Xu, Q.⁶

22
- 84879238171
- e) E. Zhang, H. Tian, S. Xu, S. Yu, Q. Xu, Org. Lett. 2013, 15, 2704-2707;
- (2013) Org. Lett. , vol.15 , pp. 2704-2707
- Zhang, E.¹ Tian, H.² Xu, S.³ Yu, S.⁴ Xu, Q.⁵

23
- 84899638384
- f) J. Wang, S. Lu, X. Cao, H. Gu, Chem. Commun. 2014, 50, 5637-5640;
- (2014) Chem. Commun. , vol.50 , pp. 5637-5640
- Wang, J.¹ Lu, S.² Cao, X.³ Gu, H.⁴

24
- 84911879472
- g) S. Zhao, C. Liu, Y. Guo, J.-C. Xiao, Q.-Y. Chen, J. Org. Chem. 2014, 79, 8926-8931.
- (2014) J. Org. Chem. , vol.79 , pp. 8926-8931
- Zhao, S.¹ Liu, C.² Guo, Y.³ Xiao, J.-C.⁴ Chen, Q.-Y.⁵

25
- 84859125801
- a) H. Huang, J. Huang, Y.-M. Liu, H.-Y. He, Y. Cao, K.-N. Fan, Green Chem. 2012, 14, 930-934;
- (2012) Green Chem. , vol.14 , pp. 930-934
- Huang, H.¹ Huang, J.² Liu, Y.-M.³ He, H.-Y.⁴ Cao, Y.⁵ Fan, K.-N.⁶

26
- 84871786367
- b) C. Su, M. Acik, K. Takai, J. Lu, S.-J. Hao, Y. Zheng, P. Wu, Q. Bao, T. Enoki, Y.-J. Chabal, K. P. Loh, Nat. Commun. 2012, 3, 1298-1306;
- (2012) Nat. Commun. , vol.3 , pp. 1298-1306
- Su, C.¹ Acik, M.² Takai, K.³ Lu, J.⁴ Hao, S.-J.⁵ Zheng, Y.⁶ Wu, P.⁷ Bao, Q.⁸ Enoki, T.⁹ Chabal, Y.-J.¹⁰ Loh, K.P.¹¹

27
- 84869188891
- c) L. Liu, Z. Wang, X. Fu, C.-H. Yan, Org. Lett. 2012, 14, 5692-5695;
- (2012) Org. Lett. , vol.14 , pp. 5692-5695
- Liu, L.¹ Wang, Z.² Fu, X.³ Yan, C.-H.⁴

28
- 84902997502
- d) H. Wang, X. Zheng, H. Chen, K. Yan, Z. Zhu, S. Yang, Chem. Commun. 2014, 50, 7517-7520.
- (2014) Chem. Commun. , vol.50 , pp. 7517-7520
- Wang, H.¹ Zheng, X.² Chen, H.³ Yan, K.⁴ Zhu, Z.⁵ Yang, S.⁶

29
- 84889025494
- a) X. Lang, X. Chen, J. Zhao, Chem. Soc. Rev. 2014, 43, 473-486.
- (2014) Chem. Soc. Rev. , vol.43 , pp. 473-486
- Lang, X.¹ Chen, X.² Zhao, J.³

30
- 84868364465
- b) J. H. Park, K. C. Ko, E. Kim, N. Park, J. H. Ko, D. H. Ryu, T. K. Ahn, J. Y. Lee, S. U. Son, Org. Lett. 2012, 14, 5502-5505;
- (2012) Org. Lett. , vol.14 , pp. 5502-5505
- Park, J.H.¹ Ko, K.C.² Kim, E.³ Park, N.⁴ Ko, J.H.⁵ Ryu, D.H.⁶ Ahn, T.K.⁷ Lee, J.Y.⁸ Son, S.U.⁹

31
- 84863116016
- c) X. Lang, W. Ma, Y. Zhao, C. Chen, H. Ji, J. Zhao, Chem. Eur. J. 2012, 18, 2624-2631;
- (2012) Chem. Eur. J. , vol.18 , pp. 2624-2631
- Lang, X.¹ Ma, W.² Zhao, Y.³ Chen, C.⁴ Ji, H.⁵ Zhao, J.⁶

32
- 84874100939
- d) S. I. Naya, K. Kimura, H. Tada, ACS Catal. 2013, 3, 10-13;
- (2013) ACS Catal. , vol.3 , pp. 10-13
- Naya, S.I.¹ Kimura, K.² Tada, H.³

33
- 84877655968
- e) N. Li, X. Lang, W. Ma, H. Ji, C. Chen, J. Zhao, Chem. Commun. 2013, 49, 5034-5036;
- (2013) Chem. Commun. , vol.49 , pp. 5034-5036
- Li, N.¹ Lang, X.² Ma, W.³ Ji, H.⁴ Chen, C.⁵ Zhao, J.⁶

34
- 84886867854
- f) W. Zhao, C. Liu, L. Cao, X. Yin, H. Xu, B. Zhang, RSC Adv. 2013, 3, 22944-22948;
- (2013) RSC Adv. , vol.3 , pp. 22944-22948
- Zhao, W.¹ Liu, C.² Cao, L.³ Yin, X.⁴ Xu, H.⁵ Zhang, B.⁶

35
- 84901586968
- g) X.-J. Yang, B. Chen, X.-B. Li, L.-Q. Zheng, L.-Z. Wu, C.-H. Tung, Chem. Commun. 2014, 50, 6664-6667;
- (2014) Chem. Commun. , vol.50 , pp. 6664-6667
- Yang, X.-J.¹ Chen, B.² Li, X.-B.³ Zheng, L.-Q.⁴ Wu, L.-Z.⁵ Tung, C.-H.⁶

36
- 85027927696
- h) L. Ye, Z. Li, ChemCatChem 2014, 6, 2540-2543;
- (2014) ChemCatChem , vol.6 , pp. 2540-2543
- Ye, L.¹ Li, Z.²

37
- 84913584742
- i) B. Yuan, R. Chong, B. Zhang, J. Liu, C. Li, Chem. Commun. 2014, 50, 15593-15596;
- (2014) Chem. Commun. , vol.50 , pp. 15593-15596
- Yuan, B.¹ Chong, R.² Zhang, B.³ Liu, J.⁴ Li, C.⁵

38
- 84907992784
- j) D. Sun, L. Ye, Z. Li, Appl. Catal. B 2015, 164, 428-432.
- (2015) Appl. Catal. B , vol.164 , pp. 428-432
- Sun, D.¹ Ye, L.² Li, Z.³

39
- 84888615985
- a) K. N. Tayade, M. Mishra, J. Mol. Catal. A 2014, 382, 114-125;
- (2014) J. Mol. Catal. A , vol.382 , pp. 114-125
- Tayade, K.N.¹ Mishra, M.²

40
- 85027945527
- b) A. Monopoli, P. Cotugno, F. Iannone, F. Ciminale, M. M. Dell'Anna, P. Mastrorilli, A. Nacci, Eur. J. Org. Chem. 2014, 5925-5931.
- (2014) Eur. J. Org. Chem. , pp. 5925-5931
- Monopoli, A.¹ Cotugno, P.² Iannone, F.³ Ciminale, F.⁴ Dell'Anna, M.M.⁵ Mastrorilli, P.⁶ Nacci, A.⁷

41
- 65649086505
- a) A. Grirrane, A. Corma, H. Garcia, J. Catal. 2009, 264, 138-144;
- (2009) J. Catal. , vol.264 , pp. 138-144
- Grirrane, A.¹ Corma, A.² Garcia, H.³

42
- 84903463638
- b) X. Qiu, C. Len, R. Luque, Y. Li, ChemSusChem 2014, 7, 1684-1688.
- (2014) ChemSusChem , vol.7 , pp. 1684-1688
- Qiu, X.¹ Len, C.² Luque, R.³ Li, Y.⁴

43
- 47749105369
- a) S.-I. Murahashi, D. Zhang, Chem. Soc. Rev. 2008, 37, 1490-1501;
- (2008) Chem. Soc. Rev. , vol.37 , pp. 1490-1501
- Murahashi, S.-I.¹ Zhang, D.²

44
- 52449135188
- b) L. Que, Jr., W. B. Tolman, Nature 2008, 455, 333-340.
- (2008) Nature , vol.455 , pp. 333-340
- Que, L.¹ Tolman, W.B.²

45
- 0037199441
- a) M. Mure, S. A. Mills, J. P. Klinman, Biochemistry 2002, 41, 9269-9278;
- (2002) Biochemistry , vol.41 , pp. 9269-9278
- Mure, M.¹ Mills, S.A.² Klinman, J.P.³

46
- 1242338900
- b) M. Mure, Acc. Chem. Res. 2004, 37, 131-139.
- (2004) Acc. Chem. Res. , vol.37 , pp. 131-139
- Mure, M.¹

47
- 84871867838
- a) M. Largeron, M.-B. Fleury, Science 2013, 339, 43-44.
- (2013) Science , vol.339 , pp. 43-44
- Largeron, M.¹ Fleury, M.-B.²

48
- 84861797419
- b) A. E. Wendlandt, S. S. Stahl, Org. Lett. 2012, 14, 2850-2853;
- (2012) Org. Lett. , vol.14 , pp. 2850-2853
- Wendlandt, A.E.¹ Stahl, S.S.²

49
- 84865639316
- c) H. Yuan, W.-J. Yoo, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2012, 134, 13970-13973;
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 13970-13973
- Yuan, H.¹ Yoo, W.-J.² Miyamura, H.³ Kobayashi, S.⁴

50
- 84910049826
- d) D. V. Jawale, E. Gravel, E. Villemin, N. Shah, V. Geertsen, I. N. N. Namboothiri, E. Doris, Chem. Commun. 2014, 50, 15251-15254.
- (2014) Chem. Commun. , vol.50 , pp. 15251-15254
- Jawale, D.V.¹ Gravel, E.² Villemin, E.³ Shah, N.⁴ Geertsen, V.⁵ Namboothiri, I.N.N.⁶ Doris, E.⁷

51
- 38849093974
- M. Largeron, A. Chiaroni, M.-B. Fleury, Chem. Eur. J. 2008, 14, 996-1003.
- (2008) Chem. Eur. J. , vol.14 , pp. 996-1003
- Largeron, M.¹ Chiaroni, A.² Fleury, M.-B.³

52
- 44049092112
- J. Piera, J.-E. Bäckvall, Angew. Chem. Int. Ed. 2008, 47, 3506-3523;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3506-3523
- Piera, J.¹ Bäckvall, J.-E.²

53
- 54749090939
- Angew. Chem. 2008, 120, 3558-3576.
- (2008) Angew. Chem. , vol.120 , pp. 3558-3576

54
- 84861493909
- M. Largeron, M.-B. Fleury, Angew. Chem. Int. Ed. 2012, 51, 5409-5412;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 5409-5412
- Largeron, M.¹ Fleury, M.-B.²

55
- 84869010659
- Angew. Chem. 2012, 124, 5505-5508.
- (2012) Angew. Chem. , vol.124 , pp. 5505-5508

56
- 0000566452
- a) Y. Yuan, X. Li, K. Ding, Org. Lett. 2002, 4, 3309-3311;
- (2002) Org. Lett. , vol.4 , pp. 3309-3311
- Yuan, Y.¹ Li, X.² Ding, K.³

57
- 0037424062
- b) C. Loncaric, K. Manabe, S. Kobayashi, Chem. Commun. 2003, 574-575;
- (2003) Chem. Commun. , pp. 574-575
- Loncaric, C.¹ Manabe, K.² Kobayashi, S.³

58
- 80052307522
- c) L. Liu, S. Zhang, X. Fu, C.-H. Yan, Chem. Commun. 2011, 47, 10148-10150.
- (2011) Chem. Commun. , vol.47 , pp. 10148-10150
- Liu, L.¹ Zhang, S.² Fu, X.³ Yan, C.-H.⁴

59
- 77954314662
- F. Bellezza, A. Cipiciani, U. Costantino, F. Fringuelli, M. Orrù, O. Piermatti, F. Pizzo, Catal. Today 2010, 152, 61-65.
- (2010) Catal. Today , vol.152 , pp. 61-65
- Bellezza, F.¹ Cipiciani, A.² Costantino, U.³ Fringuelli, F.⁴ Orrù, M.⁵ Piermatti, O.⁶ Pizzo, F.⁷

60
- 84920067709
- a) M. Ciaccia, S. Di Stefano, Org. Biomol. Chem. 2015, 13, 646-654.
- (2015) Org. Biomol. Chem. , vol.13 , pp. 646-654
- Ciaccia, M.¹ Di Stefano, S.²

61
- 84875767463
- b) M. Ciaccia, R. Cacciapaglia, P. Mencarelli, L. Mandolini, S. Di Stefano, Chem. Sci. 2013, 4, 2253-2261;
- (2013) Chem. Sci. , vol.4 , pp. 2253-2261
- Ciaccia, M.¹ Cacciapaglia, R.² Mencarelli, P.³ Mandolini, L.⁴ Di Stefano, S.⁵

62
- 84899098479
- c) M. Ciaccia, S. Pilati, R. Cacciapaglia, L. Mandolini, S. Di Stefano, Org. Biomol. Chem. 2014, 12, 3282-3287.
- (2014) Org. Biomol. Chem. , vol.12 , pp. 3282-3287
- Ciaccia, M.¹ Pilati, S.² Cacciapaglia, R.³ Mandolini, L.⁴ Di Stefano, S.⁵

63
- 84857601022
- a) M. E. Belowich, J. F. Stoddart, Chem. Soc. Rev. 2012, 41, 2003-2024.
- (2012) Chem. Soc. Rev. , vol.41 , pp. 2003-2024
- Belowich, M.E.¹ Stoddart, J.F.²

64
- 34250339758
- b) S. M. Landge, V. Atanassova, M. Thimmaiah, B. Török, Tetrahedron Lett. 2007, 48, 5161-6164.
- (2007) Tetrahedron Lett. , vol.48 , pp. 5161-6164
- Landge, S.M.¹ Atanassova, V.² Thimmaiah, M.³ Török, B.⁴

65
- 84892987286
- S. Morales, F. G. Garcia Ruano, M. B. Cid, J. Am. Chem. Soc. 2014, 136, 1082-1089.
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 1082-1089
- Morales, S.¹ Garcia Ruano, F.G.² Cid, M.B.³

66
- 33747445490
- D. Xu, A. Chiaroni, M.-B. Fleury, M. Largeron, J. Org. Chem. 2006, 71, 6374-6381.
- (2006) J. Org. Chem. , vol.71 , pp. 6374-6381
- Xu, D.¹ Chiaroni, A.² Fleury, M.-B.³ Largeron, M.⁴

67
- 0001890025
- J.-C. Zhuo, Magn. Reson. Chem. 1997, 35, 21-29.
- (1997) Magn. Reson. Chem. , vol.35 , pp. 21-29
- Zhuo, J.-C.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.