Polymeric bimetallic catalyst-promoted in-water dehydrative alkylation of ammonia and amines with alcohols

Synthesis (Germany)

Volumn 45, Issue 15, 2013, Pages 2093-2100

  Yamada, Yoichim A ^a   Ohta, Hidetoshi ^a   Yuyama, Yoshinari ^a   Uozumi, Yasuhiro ^a,b  

^a Elements Chemistry Laboratory   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

alcohols; amines; ammonia; dehydrative alkylation; polymeric boron iridium catalyst

Indexed keywords

ALKYLATING AGENTS; AQUEOUS CONDITION; HETEROBIMETALLICS; HETEROGENEOUS CATALYST; IRIDIUM CATALYST; IRIDIUM COMPLEX; N-ALKYLATION; POLYMERIC CATALYSTS;

ALCOHOLS; ALKYLATION; AMINES; AMMONIA; CATALYSTS; IRIDIUM; IRIDIUM COMPOUNDS; METALLIC COMPOUNDS;

POLYMERS;

ALCOHOL; AMINE; AMMONIA; IRIDIUM COMPLEX; POLYMER;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; DEHYDRATIVE ALKYLATION;

EID: 84880921609     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338797     Document Type: Article

References (71)

1. Alberts B., Johnson A., Lewis J., Raff M., Roberts K., Walter P. Molecular Biology of the Cell. 5th ed. Garland Science New York: 2008
2. The RNA World. Gesteland R. F., Cech T., Atkins J. F. 3rd ed. Cold Spring Harbor Laboratory Press Cold Spring Harbor: 2005
3. Organic Synthesis in Water. Grieco P. A. Blackie Academic and Professional London: 1998
4. Li C.-J. Chem. Rev.: 1993; 93 2023
5. Ishihara K. Tetrahedron: 2009; 65 1085
6. Fujita K., Yamaguchi R. Synlett: 2005; 560
7. Hamid M. H. S. A, Slatford P. A., Williams J. M. J. Adv. Synth. Catal.: 2007; 349 1555
8. Guillena G., Ramón D. J., Yus M. Angew. Chem. Int. Ed.: 2007; 46 2358
9. Nixon T. D., Whittlesey M. K. J, Williams M. J. Dalton Trans.: 2009; 753
10. Dobereiner G. E., Crabtree R. H. Chem. Rev.: 2010; 110 681
11. Guillena G., Ramón D. J., Yus M. Chem. Rev.: 2010; 110 1611
12. Watson A. J. A, Williams J. M. J. Science: 2010; 329 635
13. Crabtree R. H. Organometallics: 2011; 30 17
14. Fujita K., Yamamoto K., Yamaguchi R. Org. Lett.: 2002; 4 2691
15. Cami-Kobeci G., Slatford P. A., Whittlesey M. K., Williams J. M. J. Bioorg. Med. Chem. Lett.: 2005; 15 535
16. Eary C. T., Clausen D. Tetrahedron Lett.: 2006; 47 6899
17. Prades A., Corberán R., Poyatos M., Peris E. Chem. Eur. J.: 2008; 14 11474
18. Aramoto H., Obora Y., Ishii Y. J. Org. Chem.: 2009; 74 628
19. Chang Y.-H, Fu C.-F, Liu Y.-H, Peng S.-M, Chen J.-T, Liu S.-T. Dalton Trans.: 2009; 861
20. Blank B., Michlik S., Kempe R. Chem. Eur. J.: 2009; 15 3790
21. Liu S., Rebros M., Stephens G., Marr A. C. Chem. Commun.: 2009; 2308
22. Watanabe Y., Tsuji Y., Ohsugi Y. Tetrahedron Lett.: 1981; 22 2667
23. Murahashi S.-I, Kondo K., Hakata T. Tetrahedron Lett.: 1982; 23 229
24. Arcelli A., Khai B. T., Porzi G. J. Organomet. Chem.: 1982; 235 93
25. Watanabe Y., Tsuji Y., Ige H., Ohsugi Y., Ohta T. J. Org. Chem.: 1984; 49 3359
26. Marsella J. A. J. Org. Chem.: 1987; 52 467
27. Watanabe Y., Morisaki Y., Kondo T., Mitsudo T.-a. J. Org. Chem.: 1996; 61 4214
28. Abbenhuis R. A. T. M, Boersma J., van Koten G. J. Org. Chem.: 1998; 63 4282
29. Bitsi G., Schleiffer E., Antoni F., Jenner G. J. Organomet. Chem.: 1989; 373 343
30. Del Zotto A., Baratta W., Sandri M., Verardo G., Rigo P. Eur. J. Inorg. Chem.: 2004; 524
31. Tillack A., Hollmann D., Michalik D., Beller M. Tetrahedron Lett.: 2006; 47 8881
32. Hamid M. H. S. A, Allen C. L., Lamb G. W., Maxwell A. C., Maytum H. C., Watson A. J. A, Williams J. M. J. J. Am. Chem. Soc.: 2009; 131 1766
33. Nordstrom L. U., Madsen R. Chem. Commun.: 2007; 5034
34. Gunanathan C., Milstein D. Angew. Chem. Int. Ed.: 2008; 47 8661
35. Kawahara R., Fujita K., Yamaguchi R. J. Am. Chem. Soc.: 2010; 132 15108
36. Saidi O., Blacker A. J., Farah M. M., Marsden S. P., Williams J. M. J. Chem. Commun.: 2010; 46 1541
37. Saidi O., Blacker A. J., Lamb G. W., Marsden S. P., Taylor J. E., Williams J. M. J. Org. Process Res. Dev.: 2010; 14 1046
38. Kawahara R., Fujita K., Yamaguchi R. Adv. Synth. Catal.: 2011; 353 1161
39. Narayanan S., Deshpande K. Appl. Catal., A: 2000; 199 1
40. Valotl F., Fachel F., Jacquot R., Spagnol M., Lemairel M. Tetrahedron Lett.: 1999; 40 3689
41. Martínez R., Ramón D. J., Yus M. Org. Biomol. Chem.: 2009; 7 2176
42. Kim J. W., Yamaguchi K., Mizuno N. J. Catal.: 2009; 263 205
43. Kwon M. S., Kim S., Park S., Bosco W., Chidrala R. K., Park J. J. Org. Chem.: 2009; 74 2877
44. Yamada Y. M. A, Sarkar S. M., Uozumi Y. J. Am. Chem. Soc.: 2012; 134 9285
45. Yamada Y. M. A, Sarkar S. M., Uozumi Y. J. Am. Chem. Soc.: 2012; 134 3190
46. Sarkar S. M., Uozumi Y., Yamada Y. M. A. Angew. Chem. Int. Ed.: 2011; 50 9437
47. Yamada Y. M. A, Jin C.-K, Uozumi Y. Org. Lett.: 2010; 12 4540
48. Yamada Y. M. A, Watanabe T., Torii K., Uozumi Y. Chem. Commun.: 2009; 5594
49. Yamada Y. M. A, Guo H., Uozumi Y. Org. Lett.: 2007; 9 1501
50. Yamada Y. M. A, Uozumi Y. Tetrahedron: 2007; 63 8492
51. Uozumi Y., Yamada Y. M. A, Beppu T., Fukuyama N., Ueno M., Kitamori T. J. Am. Chem. Soc.: 2006; 128 15994
52. Yamada Y. M. A, Maeda Y., Uozumi Y. Org. Lett.: 2006; 8 4259
53. Yamada Y. M. A, Uozumi Y. Org. Lett.: 2006; 8 1375
54. Shibasaki M., Kanai M., Matsunaga S., Kumagai N. Acc. Chem. Res.: 2009; 42 1117
55. Shibasaki M., Kanai M., Funabashi K. Chem. Commun.: 2002; 1989
56. Shibasaki M., Yoshikawa N. Chem. Rev.: 2002; 102 2187
57. Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl.: 1997; 36 1236
58. Wheatley N., Kalck P. Chem. Rev.: 1999; 99 3379
59. van den Beuken E. K., Feringa B. L. Tetrahedron: 1998; 54 12985
60. Handa S., Gnanadesikan V., Matsunaga S., Shibasaki M. J. Am. Chem. Soc.: 2010; 132 4925
61. Iwata M., Yazaki R., Suzuki Y., Kumagai N., Shibasaki M. J. Am. Chem. Soc.: 2009; 131 18244
62. Nitabaru T., Nojiri A., Kobayashi M., Kumagai N., Shibasaki M. J. Am. Chem. Soc.: 2009; 131 13860
63. Wang Z., Chen G., Ding K. Chem. Rev.: 2009; 109 322
64. Lu J., Toy P. H. Chem. Rev.: 2009; 106 815
65. Takizawa S., Somei H., Jayaprakash D., Sasai H. Angew. Chem. Int. Ed.: 2003; 42 5711
66. Ding K., Wang Z., Wang X., Liang Y., Wang X. Chem. Eur. J.: 2006; 12 5188
67. Arai T., Sekiguchi T., Otsuki K., Takizawa S., Sasai H. Angew. Chem. Int. Ed.: 2003; 42 2144
68. Lang A., Knizek J., Nöth H., Schur S., Thomann M. Z. Anorg. Allg. Chem.: 1997; 623 901
69. Chikkali S. H., Gudat D., Lissner F., Nieger M., Schleid T. Dalton Trans.: 2007; 3906
70. Maki T., Ishihara K., Yamamoto H. Tetrahedron: 2007; 63 8645
71. Ishihara K., Kurihara H., Matsumoto M., Yamamoto H. J. Am. Chem. Soc.: 1998; 120 6920