Redox properties of CeO2at low temperature: The direct synthesis of imines from alcohol and amine

Angewandte Chemie - International Edition

Volumn 54, Issue 3, 2015, Pages 864-867

  Tamura, Masazumi ^a   Tomishige, Keiichi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alcohols; Amines; Cerium oxide; Imine; Redox chemistry

Indexed keywords

ALCOHOLS; AMINES; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL); TEMPERATURE;

CERIUM OXIDES; HETEROGENEOUS CATALYST; IMINE; KINETIC MEASUREMENT; LOW TEMPERATURES; ORGANIC REACTION; REACTIVE OXYGEN SPECIES; REDOX CHEMISTRY;

REDOX REACTIONS;

EID: 84920843636     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409601     Document Type: Article

References (52)

1. a) L. Vivier, D. Duprez, ChemSusChem 2010, 3, 654-678;
2. b) T. Sahu, S. S. Bisht, K. R. Das, S. Kerkar, Curr. Nanosci. 2013, 9, 588-593.
3. a) Y. Wang, F. Wang, Q. Song, Q. Xin, S. Xu, J. Xu, J. Am. Chem. Soc. 2013, 135, 1506-1515;
4. b) M. Tamura, H. Wakasugi, K.-i. Shimizu, A. Satsuma, Chem. Eur. J. 2011, 17, 11428-11431.
5. Y. Namai, K.-i. Fukui, Y. Iwasawa, J. Phys. Chem. B 2003, 107, 11666-11673.
6. F. Esch, S. Fabris, L. Zhou, T. Montini, C. Africh, P. Fornasiero, G. Comelli, R. Rosei, Science 2005, 309, 752-755.
7. a) R. D. Patil, S. Adimurthy, Asian J. Org. Chem. 2013, 2, 726-744.
8. a) K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, Angew. Chem. Int. Ed. 2003, 42, 4077-4082;
9. Angew. Chem. 2003, 115, 4211-4216;
10. b) S. Furukawa, A. Suga, T. Komatsu, Chem. Commun. 2014, 50, 3277-3280;
11. c) B. Zhu, R. J. Angelici, Chem. Commun. 2007, 2157-2159;
12. d) J. S. M. Samac, A. H. Ell, J.-E. Backvall, Chem. Eur. J. 2005, 11, 2327-2334.
13. a) X. Lang, H. Ji, C. Chen, W. Ma, J. Zhao, Angew. Chem. Int. Ed. 2011, 50, 3934-3937;
14. Angew. Chem. 2011, 123, 4020-4023;
15. b) F. Su, S. C. Mathew, L. Mohlmann, M. Antonietti, X. Wang, S. Blechert, Angew. Chem. Int. Ed. 2011, 50, 657-660;
16. Angew. Chem. 2011, 123, 683-686;
17. c) H.-A. Ho, K. Manna, A. D. Sadow, Angew. Chem. Int. Ed. 2012, 51, 8607-8610;
18. Angew. Chem. 2012, 124, 8735-8738;
19. d) M. Largeron, M.-B. Fleury, Angew. Chem. Int. Ed. 2012, 51, 5409-5412;
20. Angew. Chem. 2012, 124, 5505-5508;
21. e) S. Furukawa, Y. Ohno, T. Shishido, K. Teramura, T. Tanaka, ACS Catal. 2011, 1, 1150-1153;
22. f) A. Grirrane, A. Corma, H. Garcia, J. Catal. 2009, 264, 138-144.
23. a) E. Zhang, H. Tian, S. Xu, X. Yu, Q. Xu, Org. Lett. 2013, 15, 2704-2707;
24. b) Y.-S. Lan, B.-S. Liao, Y.-H. Liu, S.-M. Peng, S.-T. Liu, Eur. J. Org. Chem. 2013, 5160-5164;
25. c) J. W. Rigoli, S. A. Moyer, S. D. Pearce, J. M. Schomaker, Org. Biomol. Chem. 2012, 10, 1746-1749;
26. d) Q. Kang, Y. Zhang, Green Chem. 2012, 14, 1016-1019;
27. e) L. Jiang, L. Jin, H. Tian, X. Yuan, X. Yu, Q. Xu, Chem. Commun. 2011, 47, 10833-10835;
28. f) A. Maggi, R. Madsen, Organometallics 2011, 30, 451-455;
29. g) B. Gnanaprakasam, J. Zhang, D. Milstein, Angew. Chem. Int. Ed. 2010, 49, 1468-1471;
30. Angew. Chem. 2010, 122, 1510-1513;
31. h) L. Zhang, W. W. Wang, A. Wang, Y. Cui, X. Yang, Y. Huang, X. Liu, W. Liu, J.-Y. Son, H. Oji, T. Zhang, Green Chem. 2013, 15, 2680-2684;
32. i) J.-F. Soulé, H. Miyamura, S. Kobayashi, Chem. Commun. 2013, 49, 355-357;
33. j) R. R. Donthiri, R. D. Patil, S. Adimurthy, Eur. J. Org. Chem. 2012, 4457-4460;
34. k) J. Xu, R. Zhuang, L. Bao, G. Tang, Y. Zhao, Green Chem. 2012, 14, 2384-2387;
35. l) P. Liu, C. Li, E. J. M. Hensen, Chem. Eur. J. 2012, 18, 12122-12129;
36. m) J. M. Pérez, R. Cano, M. Yus, D. J. Ramón, Eur. J. Org. Chem. 2012, 4548-4554;
37. n) R. Cano, D. J. Ramon, M. Yus, J. Org. Chem. 2011, 76, 5547-5557;
38. o) W. Hei, L. Wang, C. Sun, K. Wu, S. He, J. Chen, P. Wu, Z. Yu, Chem. Eur. J. 2011, 17, 13308-13317;
39. p) S. Kegnæs, J. Mielby, U. V. Mentzel, C. H. Christensen, A. Riisager, Green Chem. 2010, 12, 1437-1441;
40. q) J. W. Kim, J. He, K. Yamaguchi, N. Mizuno, Chem. Lett. 2009, 38, 920-921;
41. r) M. S. Kwon, S. Kim, S. Park, W. Bosco, R. K. Chidrala, J. Park, J. Org. Chem. 2009, 74, 2877-2879;
42. s) H. Sun, F.-Z. Su, J. Ni, Y. Cao, H.-Y. He, K.-N. Fan, Angew. Chem. 2009, 121, 4454-4457;
43. Angew. Chem. Int. Ed. 2009, 48, 4390-4393;
44. Angew. Chem. 2009, 121, 4454-4457;
45. t) S. Sithambaram, R. Kumar, Y.-C. Son, S. L. Suib, J. Catal. 2008, 253, 269-277.
46. a) R. Severin, S. Doye, Chem. Soc. Rev. 2007, 36, 1407-1420;
47. b) A. Tillack, I. G. Castro, C. G. Hartung, M. Beller, Angew. Chem. Int. Ed. 2002, 41, 2541-2543;
48. Angew. Chem. 2002, 114, 2646-2648;
49. c) J. S. Ryu, G. Y. Li, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 12584-12605;
50. d) V. Lavallo, G. D. Frey, B. Donnadieu, M. Soleihavoup, G. Bertrand, Angew. Chem. Int. Ed. 2008, 47, 5224-5228;
51. Angew. Chem. 2008, 120, 5302-5306.
52. A. Badri, C. Binet, J.-C. Lavalley, J. Chem. Soc. Faraday Trans. 1997, 93, 1159-1168.