Microwave-assisted solventless reaction of iridium-catalyzed alkylation of amines with alcohols in the absence of base

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5386-5389

  Zhang, Weixing ^a   Dong, Xiaochun ^a   Zhao, Weili ^a,b  

^a FUDAN UNIVERSITY   (China)

^b HENAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; IRIDIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION;

ALCOHOLS; ALKYLATION; AMINES; CATALYSIS; IRIDIUM; MICROWAVES; MOLECULAR STRUCTURE;

EID: 80054722440     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202281h     Document Type: Article

References (52)

1. Lawrence, S. A. Amines: Synthesis, Properties and Applications; Cambridge University Press: Cambridge, 2005.
2. For recent reviews on borrowing hydrogen
3. Guillena, G.; Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358.
4. Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555.
5. Nixon, T. D.; Whittlesey, M. K.; Williams, J. M. J. Dalton Trans. 2009, 38, 753.
6. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681.
7. Guillena, G.; Ramón, D. J.; Yus, M. Chem. Rev. 2010, 110, 1611.
8. Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit, S.; Tongpenyai, N. J. Chem. Soc., Chem. Commun. 1981, 611.
9. Watanabe, Y.; Tsuji, Y.; Ige, H.; Ohsugi, Y.; Ohta, T. J. Org. Chem. 1984, 49, 3359.
10. Watanabe, Y.; Morisaki, Y.; Kondo, T.; Mitsudo, T.-A. J. Org. Chem. 1996, 61, 4214.
11. Ganguly, S.; Roundhill, D. M. Polyhedron 1990, 20, 2517.
12. Huh, K.-T.; Tsuji, Y.; Kobayashi, M.; Okuda, F.; Watanabe, Y. Chem. Lett. 1988, 449.
13. Naskar, S.; Bhattacharjee, M. Tetrahedron Lett. 2007, 48, 3367.
14. Hamid, M. H. S. A.; Williams, J. M. J. Chem. Commun. 2007, 725.
15. Hamid, M. H. S. A.; Williams, J. M. J. Tetrahedron Lett. 2007, 48, 8263.
16. Hollmann, D.; Tillack, A.; Michalik, D.; Jackstell, R.; Beller, M. Chem.-Asian J. 2007, 2, 403.
17. Tillack, A.; Hollmann, D.; Michalik, D.; Beller, M. Tetrahedron Lett. 2006, 47, 8881.
18. Del Zotto, A.; Baratta, W.; Sandri, M.; Verardo, G.; Rigo, P. Eur. J. Inorg. Chem. 2004, 524.
19. Gunanathan, V; Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661.
20. Imm, S.; Bähn, S.; Neubert, L.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 8126.
21. For a very recent review
22. Suzuki, T. Chem. Rev. 2011, 111, 1825 and references cited therein.
23. Cami-Kobeci, G.; Williams, J. M. J. Chem. Commun. 2004, 1072.
24. Cami-Kobeci, G.; Slatford, P. A.; Whittlesey,M. K.; Williams, J. M. J. Bioorg. Med. Chem. Lett. 2005, 15, 535.
25. Nordstrøm, L. U.; Madsen, R. Chem. Commun. 2007, 5034.
26. Blank, B.; Madalska, M.; Kempe, R. Adv. Synth. Catal. 2008, 350, 749.
27. Gunanathan, C.; Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661.
28. Prades, A.; Corberán, R.; Poyatos, M.; Peris, E. Chem.-Eur. J. 2008, 14, 11474.
29. Gnanamgari, D.; Sauer, E. L. O.; Schley, N. D.; Butler, C.; Incarvito, C. D.; Crabtree, R. H. Organometallics 2009, 28, 321.
30. Blank, B.; Michlik, S.; Kempe, R. Chem.-Eur. J. 2009, 15, 3790.
31. Michlik, S.; Kempe, R. Chem.-Eur. J. 2010, 16, 13193.
32. Tanaka, N.; Hatanaka, M.; Watanabe, Y. Chem. Lett. 1992, 575.
33. Tsuji, R.; Takeuchi, Y.; Ogawa, H.; Watanabe, Y. Chem. Lett. 1986, 293.
34. Fujita, K.; Li, Z.; Yamaguchi, R. Tetrahedron Lett. 2003, 44, 2687.
35. Fujita, K.-I.; Yamaguchi, R. Synlett 2005, 4, 560.
36. Fujita, K.-I.; Enoki, Y.; Yamaguchi, R. Org. Synth. 2006, 83, 217.
37. Fujita, K.-I.; Enoki, Y.; Yamaguchi, R. Tetrahedron 2008, 64, 1943.
38. Yamaguchi, R.; Kawagoe, S.; Asai, C.; Fujita, K.-I. Org. Lett. 2008, 10, 181.
39. Yamaguchi, R.; Mingwen, Z.; Kawagoe, S.; Asai, C.; Fujita, K.-I. Synthesis 2009, 1220.
40. Nordstrøm, L. U.; Madsen, R. Chem. Commun. 2007, 5034.
41. 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.
42. Saidi, O.; Blacker, A. J.; Farah, M. M.; Marsden, S. P.; Williams, J. M. J. Chem. Commun. 2010, 1541.
43. Blank, B.; Madalska, M; Kempe, R. Adv. Synth. Catal. 2008, 350, 749.
44. Blank, B.; Michlik, S.; Kempe, R. Chem.-Eur. J. 2009, 15, 3790.
45. Kawahara, R.; Fujita, K.-I.; Yamaguchi, R. J. Am. Chem. Soc. 2010, 132, 15108.
46. Grigg, R.; Whitney, S.; Sridharan, V.; Keep, A.; Derrick, A. Tetrahedron 2009, 65, 4375.
47. Löfberg, C.; Grigg, R.; Whittaker, M. A.; Keep, A.; Derrick, A. J. Org. Chem. 2006, 71, 8023.
48. Anxionnat, B.; Pardo, D. G.; Ricci, G.; Cossy, J. Org. Lett. 2011, 13, 4084.
49. Lubinu, M. C.; De Luca, L.; Giacomelli, G.; Porcheddu, A. Chem.-Eur. J. 2011, 17, 82.
50. Watson, A. J. A.; Maxwell, A. C.; Williams, J. M. J. J. Org. Chem. 2011, 76, 2328. Iridium has been mentioned in the footnote to be effective; however, no details have been reported.
51. Fujita, K.-I.; Yamamoto, K.; Yamaguchi, R. Org. Lett. 2004, 6, 3525.
52. Prades, A.; Corberán, R.; Poyatos, M.; Peris, E. Chem.; Eur. J. 2008, 14, 11474.