Continuous synthesis and use of N-heterocyclic carbene copper(I) complexes from insoluble Cu2O

Organic Letters

Volumn 15, Issue 5, 2013, Pages 996-999

  Opalka, Suzanne M ^a,b   Park, Jin Kyoon ^a,c   Longstreet, Ashley R ^a   McQuade, D Tyler ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

^b Department of Obstetrics Gynecology   (United States)

^c Pusan National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84874608367     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303442m     Document Type: Article

References (43)

1. Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686
2. Anastas, P. T.; Kirchhoff, M. M.; Williamson, T. C. Appl. Catal,. A 2001, 221, 3
3. Wiles, C.; Watts, P. Chem. Commun. 2011, 47, 6512
4. Wegner, J.; Ceylan, S.; Kirschning, A. Chem. Commun. 2011, 47, 4583
5. Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Chem. Rev. 2007, 107, 2300
6. Watts, P.; Haswell, S. J. Chem. Eng. Technol. 2005, 28, 290
7. Pennemann, H.; Watts, P.; Haswell, S. J.; Hessel, V.; Löwe, H. Org. Process Res. Dev. 2004, 8, 422
8. Watts, P.; Haswell, S. J. Drug Discovery Today 2003, 8, 586
9. Löwe, H.; Ehrfeld, W. Electrochim. Acta 1999, 44, 3679
10. Newton, S.; Ley, S. V.; Arcé, E. C.; Grainger, D. M. Adv. Synth. Catal. 2012, 354, 1805
11. Noël, T.; Musacchio, A. J. Org. Lett. 2011, 13, 5180
12. Mercadante, M. A.; Leadbeater, N. E. Org. Biomol. Chem. 2011, 9, 6575
13. Zhang, Y.; Jamison, T. F.; Patel, S.; Mainolfi, N. Org. Lett. 2010, 13, 280
14. Tagata, T.; Nishida, M.; Nishida, A. Adv. Synth. Catal. 2010, 352, 1662
15. Kobayashi, J.; Mori, Y.; Kobayashi, S. Adv. Synth. Catal. 2005, 347, 1889
16. Saaby, S.; Knudsen, K. R.; Ladlow, M.; Ley, S. V. Chem. Commun. 2005, 2909
17. Park, J. K.; McQuade, D. T. Synthesis 2012, 44, 1485
18. Park, J. K.; McQuade, D. T. Angew. Chem., Int. Ed. 2012, 51, 2717
19. Park, J. K.; Ondrusek, B. A.; McQuade, D. T. Org. Lett. 2012, 14, 4790
20. Park, J. K.; Lackey, H. H.; Ondrusek, B. A.; McQuade, D. T. J. Am. Chem. Soc. 2011, 133, 2410
21. Park, J. K.; Lackey, H. H.; Rexford, M. D.; Kovnir, K.; Shatruk, M.; McQuade, D. T. Org. Lett. 2010, 12, 5008
22. Noel, T.; Naber, J. R.; Hartman, R. L.; McMullen, J. P.; Jensen, K. F.; Buchwald, S. L. Chem. Sci. 2011, 2, 287
23. Browne, D. L.; Deadman, B. J.; Ashe, R.; Baxendale, I. R.; Ley, S. V. Org. Process Res. Dev. 2011, 15, 693
24. Kelly, C. B.; Lee, C.; Leadbeater, N. E. Tetrahedron Lett. 2011, 52, 263
25. Shu, W.; Pellegatti, L.; Oberli, M. A.; Buchwald, S. L. Angew. Chem. Int., Ed. 2011, 50, 10665
26. Opalka, S. M.; Longstreet, A. R.; McQuade, D. T. Beilstein J. Org. Chem. 2011, 7, 1671
27. Horie, T.; Sumino, M.; Tanaka, T.; Matsushita, Y.; Ichimura, T.; Yoshida, J.-i. Org. Process Res. Dev. 2010, 14, 405
28. Sedelmeier, J.; Ley, S. V.; Baxendale, I. R.; Baumann, M. Org. Lett. 2010, 12, 3618
29. Jongen, N.; Donnet, M.; Bowen, P.; Lemaiître, J.; Hofmann, H.; Schenk, R.; Hofmann, C.; Aoun-Habbache, M.; Guillemet-Fritsch, S.; Sarrias, J.; Rousset, A.; Viviani, M.; Buscaglia, M. T.; Buscaglia, V.; Nanni, P.; Testino, A.; Herguijuela, J. R. Chem. Eng. Technol. 2003, 26, 303
30. Pedrick, E. A.; Leadbeater, N. E. Inorg. Chem. Commun. 2011, 14, 481
31. Sai, M.; Yorimitsu, H.; Oshima, K. Angew. Chem. Int., Ed. 2011, 50, 3294
32. Boogaerts, I. I. F.; Fortman, G. C.; Furst, M. R. L.; Cazin, C. S. J.; Nolan, S. P. Angew. Chem. Int., Ed. 2010, 49, 8674
33. Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
34. Lin, J. C. Y.; Huang, R. T. W.; Lee, C. S.; Bhattacharyya, A.; Hwang, W. S.; Lin, I. J. B. Chem. Rev. 2009, 109, 3561
35. Diez-Gonzalez, S.; Nolan, S. P. Aldrichimica Acta 2008, 41, 43
36. Douthwaite, R. E. Coord. Chem. Rev. 2007, 251, 702
37. Díez-González, S.; Nolan, S. P. Synlett 2007, 2007, 2158
38. Landers, B.; Navarro, O. Eur. J. Inorg. Chem. 2012, 2012, 2980
39. Note: This example inspired this work. Citadelle, C. A.; Nouy, E. L.; Bisaro, F.; Slawin, A. M. Z.; Cazin, C. S. J. Dalton Trans. 2010, 39, 4489
40. Chun, J.; Lee, H. S.; Jung, I. G.; Lee, S. W.; Kim, H. J.; Son, S. U. Organometallics 2010, 29, 1518
41. For more information, see: http://www.vapourtec.co.uk/home.
42. Tulloch, A. A. D.; Danopoulos, A. A.; Kleinhenz, S.; Light, M. E.; Hursthouse, M. B.; Eastham, G. Organometallics 2001, 20, 2027
43. For an inexpensive flow device, see: Quevedo, E.; Steinbacher, J.; McQuade, D. T. J. Am. Chem. Soc. 2005, 127, 10498