Palladium-catalyzed hydrodehalogenation of aryl halides using paraformaldehyde as the hydride source: High-throughput screening by paper-based colorimetric iodide sensor

Tetrahedron Letters

Volumn 54, Issue 38, 2013, Pages 5207-5210

  Pyo, Ayoung ^a   Kim, Sudeok ^b   Kumar, Manian Rajesh ^a   Byeun, Aleum ^a   Eom, Min Sik ^b   Han, Min Su ^b   Lee, Sunwoo ^a  

^a Chonnam National University   (South Korea)

^b Chung Ang University   (South Korea)

Author keywords

Aryl bromides; Aryl iodides; High throughput screening; Hydrodehalogenation; Palladium

Indexed keywords

BASE; BROMIDE; GOLD NANOPARTICLE; HALIDE; IODIDE; PALLADIUM; PARAFORMALDEHYDE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CATALYSIS; COLORIMETRY; DEHALOGENATION; GAS CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; PAPER;

EID: 84881611256     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.071     Document Type: Article

References (48)

1. M.T. Reetz Angew. Chem., Int. Ed. 41 2002 1335 1338
2. J.P. Stambuli, and J.F. Hartwig Curr. Opin. Chem. Biol. 7 2003 420 426
3. G.D. Cremer, B.F. Sels, D.E. De Vos, J. Hofkens, and M.B. Roeffaers Chem. Soc. Rev. 39 2010 4703 4717
4. P. Vicennati, N. Bensel, A. Wagner, C. Créminon, and F. Taran Angew. Chem., Int. Ed. 44 2005 6863 6866
5. R.V. Rozhkov, V.J. Davisson, and D.E. Bergstrom Adv. Synth. Catal. 350 2008 71 75
6. J.P. Stambuli, S.R. Stauffer, K.H. Shaughnessy, and J.F. Hartwig J. Am. Chem. Soc. 123 2001 2677 2678
7. V. Sashuk, D. Schoeps, and H. Plenio Chem. Commun. 2009 770 772
8. E. Jung, S. Kim, Y. Kim, S.H. Seo, S.S. Lee, M.S. Han, and S. Lee Angew. Chem., Int. Ed. 50 2011 4386 4389
9. S. Kim, E. Jung, M.J. Kim, A. Pyo, T. Palani, M.S. Eom, M.S. Han, and S. Lee Chem. Commun. 48 2012 8751 8753
10. P. Selvam, S.K. Mohapatra, S.U. Sonavane, and R.V. Jayaram Appl. Catal. B 49 2004 251 255
11. W. Zhou, D. Fu, and Z. Sun Res. Environ. Sci. 6 1991 9 12
12. C.E. Castro Rev. Environ. Contam. Toxicol. 155 1998 1 67
13. M.J. Morra, V. Borek, and J. Koolpe J. Environ. Qual. 29 2000 706 715
14. P.J. Morris, W.W. Mohn, J.F. Quenson, J.M. Tiedje, and S.A. Boyd Appl. Environ. Microbiol. 58 1992 3088 3094
15. V. Dichiarante, M. Fagnoni, and A. Albini Green Chem. 11 2009 942 945
16. Y. Shiraishi, Y. Takeda, Y. Sugano, S. Ichikawa, S. Tanaka, and T. Hirai Chem. Commun. 47 2011 7863 7865
17. S.H. Leung, D.G. Edington, T.E. Griffith, and J.J. James Tetrahedron Lett. 40 1999 7189 7191
18. M.S. Viciu, G.A. Grasa, and S.P. Nolan Organometallics 20 2001 3607 3612
19. A. Arcadi, G. Cerichelli, M. Chiarini, R. Vico, and D. Zorzan Eur. J. Org. Chem. 16 2004 3404 3407
20. O. Navarro, N. Marion, Y. Oonishi, R.A. Kelly III, and S.P. Nolan J. Org. Chem. 71 2006 685 692
21. N. Iranpoor, H. Firouzabadi, and R. Azadi J. Organomet. Chem. 695 2010 887 890
22. Y. Huang, S. Liu, Z. Lin, W. Li, X. Li, and R. Cao J. Catal. 292 2012 111 117
23. H. Guo, K.-I. Kannao, and T. Takahashi Chem. Lett. 33 2004 1356
24. W.M. Czaplik, S. Grupe, M. Mayer, and A.J. von Wangelin Chem. Commun. 46 2010 6350 6352
25. Z. Zhang, N. Cissoko, J. Wo, and X. Xu J. Hazard. Mater. 165 2009 78 86
26. K. Fujita, M. Owaki, and R. Yamaguchi Chem. Commun. 2002 2964 2965
27. M.L. Buil, M.A. Esteruelas, S. Niembro, M. Oliván, L. Orzechowski, C. Pelayo, and A. Vallribera Organometallics 29 2010 4375 4383
28. S. Kuhl, R. Schneider, and Y. Fort Adv. Synth. Catal. 345 2003 341 344
29. C. Desmarets, S. Kuhl, R. Schneider, and Y. Fort Organometallics 21 2002 1554 1559
30. K. Mochizuki, and M. Suzuki Inorg. Chem. Commun. 14 2011 902 905
31. T. Hara, K. Mori, M. Oshiba, T. Mizugaki, K. Ebitani, and K. Kaneda Green Chem. 6 2004 507 509
32. Y. Monguchi, A. Kume, K. Hattori, T. Maegawa, and H. Sajiki Tetrahedron 62 2006 7926 7933
33. A. Kume, Y. Monguchi, K. Hattori, H. Nagase, and H. Sajiki Appl. Catal., B Environ. 81 2008 274 282
34. F. Chang, H. Kim, B. Lee, H.G. Park, and J. Park Bull. Korean Chem. Soc. 32 2011 1074 1076
35. J. Chen, Y. Zhang, L. Yang, X. Zhang, J. Liu, L. Li, and H. Zhang Tetrahedron 63 2007 4266 4270
36. J. Moon, and S. Lee J. Organomet. Chem. 694 2009 473 477
37. G. Chelucci Tetrahedron Lett. 51 2010 1562 1565
38. X.-J. Wang, L. Zhang, H. Lee, N. Haddad, D. Krishnamurthy, and C.H. Senanayake Org. Lett. 11 2009 5026 5028
39. N.A. Cortese, and R.F. Heck J. Org. Chem. 42 1977 3491 3494
40. A.M. Zawisza, and J. Muzart Tetrahedron Lett. 48 2007 6738 6742
41. J. Yang, and M. Brookhart J. Am. Chem. Soc. 129 2007 12656 12657
42. P.P. Cellier, J.-F. Spindler, M. Taillefer, and H.-J. Cristau Tetrahedron Lett. 44 2003 7191 7195
43. C. Li, L. Wang, P. Li, and W. Zhou Chem. Eur. J. 17 2011 10208 10212
44. C.-W. Chan, Z. Zhou, A.S.C. Chan, and W.-Y. Yu Org. Lett. 12 2010 3926 3929
45. L. Adak, S. Bhadra, and B.C. Ranu Tetrahedron Lett. 51 2010 3811 3814
46. E. Schmidt Ber. Dtsch. Chem. Ges. 52 1919 400 413
47. G.R. Heal, and L.L. Mkayula Carbon 26 1988 815 823
48. H. Jin, S.-E. Park, J.M. Lee, and S.K. Ryu Carbon 34 1996 429 431