Continuous recycling of homogeneous Pd/Cu catalysts for cross-coupling reactions

Organic Letters

Volumn 16, Issue 15, 2014, Pages 3974-3977

  Sharma, Siddharth ^a   Basavaraju, K C ^b   Singh, Ajay K ^b   Kim, Dong Pyo ^b  

^a GURU NANAK DEV UNIVERSITY   (India)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84905400530     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501802w     Document Type: Article

References (55)

1. Clark, J. H. Nat. Chem. 2009, 1, 12
2. Elvira, K. S.; Solvas, X. C.; Wootton, R. C. R.; deMello, A. J. Nat. Chem. 2013, 5, 905
3. Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385
4. Cole-Hamilton, D. J. Science 2003, 299, 1702
5. Molnár, á. Chem. Rev. 2011, 111, 2251
6. Gates, B. C. Catalytic Chemistry; Wiley-Interscience: New York, 1991; Chapter 6.
7. Durán, P. L.; Rothenberg, G. Appl. Organometal. Chem. 2008, 22, 288
8. Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345
9. Behr, A.; Henze, G.; Johnen, L.; Awungacha, C. J. Mol. Catal. A: Chem. 2008, 285, 20
10. Behr, A.; Henze, G.; Obst, D.; Turkowski, B. Green Chem. 2005, 7, 645
11. Bergbreiter, D. E.; Liu, Y.-S.; Osburn, P. L. J. Am. Chem. Soc. 1998, 120, 4250
12. Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058
13. Bergbreiter, D. E.; Osburn, P. L.; Smith, T.; Li, C.; Frels, J. D. J. Am. Chem. Soc. 2003, 125, 6254
14. Bergbreiter, D. E.; Hamilton, P. N.; Koshti, N. M. J. Am. Chem. Soc. 2007, 129, 10666
15. Brunsch, Y.; Behr, A. Angew. Chem., Int. Ed. 2013, 52, 1586
16. Bergbreiter, D. E.; Weatherford, D. A. J. Org. Chem. 1989, 54, 2726
17. Whitesides, G. Nature 2006, 442, 368
18. Cantillo, D.; Baghbanzadeh, M.; Kappe, C. O. Angew. Chem., Int. Ed. 2012, 51, 10190
19. Rodrigues, T.; Schneider, P.; Schneider, G. Angew. Chem., Int. Ed. 2014, 53, 5750
20. Shu, W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2012, 51, 5355
21. Lévesque, F.; Seeberger, P. H. Angew. Chem., Int. Ed. 2012, 51, 1706
22. Noël, T.; Buchwald, S. L. Chem. Soc. Rev. 2011, 40, 5010
23. Wegner, J.; Ceylan, S.; Kirschning, A. Chem. Commun. 2011, 47, 4583
24. Wiles, C.; Watts, P. Chem. Commun. 2011, 47, 6512
25. Hessel, V.; Kralisch, D.; Kockmann, N.; Noël, T.; Wang, Q. ChemSusChem 2013, 6, 746
26. Mastronardi, F.; Gutmann, B.; Kappe, C. O. Org. Lett. 2013, 15, 5590
27. Wirth, T. ChemSusChem 2012, 5, 215
28. Opalka, S. M.; Park, J. K.; Longstreet, A. R.; McQuade, D. T. Org. Lett. 2013, 15, 996
29. Theberge, A. B.; Whyte, G.; Frenzel, M.; Fidalgo, L. M.; Wootton, R. C. R.; Huck, W. T. S. Chem. Commun. 2009, 6225
30. Liu, S.; Fukuyama, T.; Sato, M.; Ryu, I. Org. Process Res. Dev. 2004, 8, 477
31. Solodenko, W.; Mennecke, K.; Vogt, C.; Gruhl, S.; Kirschning, A. Synthesis 2006, 1873
32. Mennecke, K.; Solodenko, W.; Kirschning, A. Synthesis 2008, 1589
33. Li, P.; Moore, J. S.; Jensen, K. F. ChemCatChem 2013, 5, 1729
34. Fukuyama, T.; Rahman, M. T.; Sumino, Y.; Ryu, I. Synlett 2012, 23, 227
35. Fukuyama, T.; Rahman, M. T.; Kamata, N.; Tokizane, M.; Fukuda, Y.; Ryu, I. J. Flow Chem. 2013, 3, 4
36. Schafer, E.; Brunsch, Y.; Sadowski, G.; Behr, A. Ind. Eng. Chem. Res. 2012, 51, 10296
37. Marchetti, A.; Preti, C.; Tagliazucchi, M. J. Chem. Eng. Data 1991, 36, 360
38. Bergbreiter, D. E.; Hughes, R.; Besinaiz, J.; Li, C.; Osburn, P. L. J. Am. Chem. Soc. 2003, 125, 8244
39. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309
40. Vlaar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem., Int. Ed. 2013, 52, 7084
41. Vlaar, T.; Cioc, R. C.; Mampuys, P.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. Angew. Chem., Int. Ed. 2012, 51, 13058
42. DeRuiter, J.; Brubaker, A. N.; Millen, J.; Riley, T. N. J. Med. Chem. 1986, 29, 627
43. Glorius, F. N-Heterocyclic Carbenes in Transition Metal Catalysis Series: Topics in Organometallic Chemistry; Springer: Berlin, 2007; pp 22-30.
44. Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997
45. Karimi, B.; Enders, D. Org. Lett. 2006, 8, 1237
46. Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314
47. Sharma, S.; Maurya, R. A.; Min, K.-I.; Jeong, G.-Y.; Kim, D.-P. Angew. Chem., Int. Ed. 2013, 52, 7564
48. Hajduk, P. J. Nature 2011, 470, 42
49. Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440
50. Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031
51. Cyr, P.; Deng, S. T.; Hawkins, J. M.; Price, K. E. Org. Lett. 2013, 15, 4342
52. King, A. O.; Corley, E. G.; Anderson, R. K.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1993, 58, 3731
53. Yamada, Y. M. A.; Sarkar, S. M.; Uozumi, Y. J. Am. Chem. Soc. 2012, 134, 6243
54. Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833
55. Gao, Y.; Wang, G.; Chen, L.; Xu, P.; Zhao, Y.; Zhou, Y.; Han, L.-B. J. Am. Chem. Soc. 2009, 131, 7956