Greening the Wacker process

Tetrahedron Letters

Volumn 54, Issue 19, 2013, Pages 2293-2295

  Kulkarni, Mukund G ^a   Shaikh, Yunnus B ^a   Borhade, Ajit S ^a   Chavhan, Sanjay W ^a   Dhondge, Attrimuni P ^a   Gaikwad, Dnyaneshwar D ^a   Desai, Mayur P ^a   Birhade, Deekshaputra R ^a   Dhatrak, Nagorao R ^a  

^a UNIVERSITY OF PUNE   (India)

Author keywords

Palladium; Potassium bromate; Terminal olefin; Wacker oxidation

Indexed keywords

ALKENE; COPPER CHLORIDE; PALLADIUM; POTASSIUM BROMATE;

ARTICLE; CATALYST; CHEMICAL REACTION; WACKER OXIDATION;

EID: 84875963473     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.082     Document Type: Article

References (60)

1. R.A. Sheldon C.R. Acad. Sci. Paris, Hc, Chim./Chem. 3 2000 541
2. R.A. Sheldon CHEMTECH 1994 38
3. F.C.Z. Phillips Anorg. Chem. 6 1894 213
4. J. Smidt, W. Hafner, R. Jira, R. Sieber, J. Sedlmeier, and A. Sabel Angew. Chem. 74 1962 93
5. W.H. Clement, and C.M. Selwitz J. Org. Chem. 29 1964 241
6. J. Tsuji Synthesis 1984 369
7. J. Auge Green Chem. 10 2008 225
8. W.H. Clement, and C.M. Selwitz J. Org. Chem. 29 1964 241
9. H. Mimoun, R. Charpentier, A. Mitschler, J. Fischer, and R. Weiss J. Am. Chem. Soc. 102 1980 1047
10. M. Roussel, and H. Mimoun J. Org. Chem. 45 1980 5387
11. A. Harada, Y. Hu, and S. Takahashi Chem. Lett. 15 1986 2083
12. H.A. Zahalka, K. Januszkiewicz, and H. Alpe J. Mol. Catal. A: Chem. 35 1986 249
13. J. Tsuji, and M. Minato Tetrahedron Lett. 28 1987 3683
14. J.-E. Backvall, and R.B. Hopkins Tetrahedron Lett. 29 1988 2885
15. J. Nokami, H. Ogawa, S. Miyamoto, T. Mandai, S. Wakabayashi, and J. Tsuji Tetrahedron Lett. 29 1988 5181
16. J.-E. Backvall, R.B. Hopkins, H. Grennberg, M.M. Mader, and A.K. Awasthi J. Am. Chem. Soc. 112 1990 5160
17. D.G. Miller, and D.D.M. Wayner J. Org. Chem. 55 1990 2924
18. E. Monflier, E. Blouet, Y. Barbaux, and A. Mortreux Angew. Chem., Int. Ed. Engl. 33 1994 2100
19. J.-H. Ahn, and D.C. Sherrington Macromolecules 29 1996 4164
20. A.W. Stobbe-Kreemers, M. van der Zon, M. Makkee, and J.J.F. Scholten J. Mol. Catal. A: Chem. 107 1996 247
21. G.-J. ten Brink, I.W.C.E. Arends, G. Papadogianakis, and R.A. Sheldon Chem. Commun. 1998 2359
22. B. Betzemeier, F. Lhermitte, and P. Knochel Tetrahedron Lett. 39 1998 6667
23. G.-J. ten Brink, I.W.C.E. Arends, G. Papadogianakis, and R.A. Sheldon Appl. Catal., A 194-195 2000 435 442
24. E. Karakhanov, A. Maximov, and A. Kirillov J. Mol. Catal. A: Chem. 157 2000 25 30
25. T. Nishimura, N. Kakiuchi, T. Onoue, K. Ohe, and S. Uemura J. Chem. Soc., Perkin Trans. 1 2000 1915
26. E. Karakhanov, T. Buchneva, A. Maximov, and M. Zavertyaeva J. Mol. Catal. A: Chem. 184 2002 11 17
27. T. Yokota, A. Sakakura, M. Tani, S. Sakaguchi, and Y. Ishii Tetrahedron Lett. 43 2002 8887
28. K.-M. Choi, T. Mizugaki, K. Ebitani, and K. Kaneda Chem. Lett. 32 2003 180
29. A.L. Maksimov, T.S. Buchneva, and E.A. Karakhanov J. Mol. Catal. A: Chem. 217 2004 59 67
30. C.N. Cornell, and M.S. Sigman J. Am. Chem. Soc. 127 2005 2796
31. T. Mitsudome, T. Umetani, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda Tetrahedron Lett. 47 2006 1425
32. T. Mitsudome, T. Umetani, N. Nosaka, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda Angew. Chem., Int. Ed. 45 2006 481
33. V.V. Potekhinand, and V.A. Matsura Russ. Chem. Bull., Int. Ed. 55 2006 650
34. J.-Q. Wang, F. Cai, E. Wang, and L.-N. He Green Chem. 9 2007 882
35. E.A. Karakhanov, A.L. Maksimov, E.A. Runova, Y.S. Kardasheva, M.V. Terenina, S.V. Kardashev, V.A. Skorkin, L.M. Karapetyan, and M.Y. Talanova Russ. Chem. Bull., Int. Ed. 57 2008 780
36. A.L. Miller II, and N.B. Bowden J. Org. Chem. 74 2009 4834
37. J. Ettedgui, and R. Neumann J. Am. Chem. Soc. 131 2009 4
38. E.A. Karakhanov, A.L. Maximov, B.N. Tarasevich, and V.A. Skorkin J. Mol. Catal. A: Chem. 297 2009 73
39. J.-L. Wang, L.-N. He, C.-X. Miao, and Y.-N. Li Green Chem. 11 2009 1317
40. B.W. Michel, A.M. Camelio, C.N. Cornell, and M.S. Sigman J. Am. Chem. Soc. 131 2009 6076
41. T. Mitsudome, K. Mizumoto, T. Mizugaki, K. Jitsukawa, and K. Kaneda Angew. Chem., Int. Ed. 49 2010 1238
42. C.N. Cornell, and M.S. Sigman Org. Lett. 8 2006 4117
43. A. Naik, L. Meina, M. Zabel, and O. Reiser Chem. Eur. J. 16 2010 1624
44. B.W. Michel, J.R. McCombs, A. Winkler, and M.S. Sigman Angew. Chem., Int. Ed. 49 2010 7312
45. L.A. Berben, D.C. Craig, C. Gimbert-Suriñach, A. Robinson, K.H. Sugiyarto, and S.B. Colbran Inorg. Chim. Acta 370 2011 374
46. J.R. McCombs, B.W. Michel, and M.S. Sigman J. Org. Chem. 76 2011 3609
47. M.G. Kulkarni, S.M. Bagale, M.P. Shinde, D.D. Gaikwad, A.S. Borhade, A.P. Dhondge, S.W. Chavhan, Y.B. Shaikh, V.B. Ningdale, M.P. Desai, and D.R. Birhade Tetrahedron Lett. 50 2009 2893
48. D.B. Rydberg, and J. Meinwald Tetrahedron Lett. 37 1996 1129
49. S. Srivastava, H. Tripathi, and K. Singh Transition Met. Chem. 26 2001 727
50. S.M. Desai, N.N. Halligudi, and S.T. Nandibewoor Transition Met. Chem. 27 2002 207
51. B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, Z. Zaghaghi, and A. Hazar Acta Chim. Slov. 50 2003 563
52. F. Shirini, M.A. Zolfigoland, and M. Khaleghi Phosphorus, Sulfur Silicon Relat. Elem. 178 2003 2107
53. S. Bhat, A.R. Ramesh, and S. Chandrasekaran Synlett 1995 329
54. M. Adinolfi, G. Barone, L. Guariniello, and A. Iadonisi Tetrahedron Lett. 40 1999 8439
55. P.M. Senthilkumar, A. Aravind, and S. Baskaran Tetrahedron Lett. 48 2007 1175
56. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277
57. B. Zeynizadeh, K.A. Dilmaghani, and A. Roozijoy Synth. Commun. 35 2005 557
58. E. McNeill, and J.D. Bois J. Am. Chem. Soc. 132 2010 10202
59. For a review on aldehyde formation through Wacker oxidation, see: J. Muzart Tetrahedron 63 2007 7505
60. B. Weiner, A. Baeza, T. Jerphagnon, and B.L. Feringa J. Am. Chem. Soc. 131 2009 9473