Ruthenium-catalyzed redox isomerization/transfer hydrogenation in organic and aqueous media: A one-pot tandem process for the reduction of allylic alcohols

Green Chemistry

Volumn 11, Issue 12, 2009, Pages 1992-2000

  Cadierno, Victorio ^a   Crochet, Pascale ^a   Francos, Javier ^a   García Garrido, Sergio E ^a   Gimeno, José ^a   Nebra, Noel ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 71549139771     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b916117a     Document Type: Article

References (119)

1. See, for example: L. F. Tietze Chem. Rev. 1996 96 115.
2. S. F. Mayer W. Kroutil K. Faber Chem. Soc. Rev. 2001 30 332.
3. J. M. Lee Y. Na H. Han S. Chang Chem. Soc. Rev. 2004 33 302.
4. Some examples of illustrative reviews on metal-catalyzed tandem processes: G. A. Molander C. R. Harris Chem. Rev. 1996 96 307.
5. P. Eilbracht L. Bärfacker C. Buss C. Hollmann E. Kitsos-Rzychon C. L. Kranemann T. Rische R. Roggenbuck A. Schmidt Chem. Rev. 1999 99 3329.
6. G. Poli G. Giambastiani A. Heumann Tetrahedron 2000 56 5959.
7. S.-I. Ikeda Acc. Chem. Res. 2000 33 511.
8. S. F. Mayer W. Kroutil K. Faber Chem. Soc. Rev. 2001 30 332.
9. J.-C. Wasilke S. J. Obrey R. T. Baker G. C. Bazan Chem. Rev. 2005 105 1001.
10. C. Bruneau S. Dérien P. H. Dixneuf Top. Organomet. Chem. 2006 19 295.
11. For a highly formative review on tandem catalysis see: D. E. Fogg E. N. dos Santos Coord. Chem. Rev. 2004 248 2365.
12. For recent reviews, see: S. E. Clapman A. Hadzovic R. H. Morris Coord. Chem. Rev. 2004 248 2201.
13. S. Gladiali A. Alberico Chem. Soc. Rev. 2006 35 226.
14. J. S. M. Samec J.-E. Bäckvall P. G. Andersson P. Brandt Chem. Soc. Rev. 2006 35 237.
15. T. Ikariya A. J. Blacker Acc. Chem. Res. 2007 40 1300.
16. For recent examples of highly efficient catalysts, see: W. Baratta G. Chelucci S. Gladiali K. Siega M. Toniutti M. Zanette E. Zangrando P. Rigo Angew. Chem., Int. Ed. 2005 44 6214.
17. W. Baratta K. Siega P. Rigo Adv. Synth. Catal. 2007 349 1633.
18. W. Baratta M. Ballico G. Esposito P. Rigo Chem.–Eur. J. 2008 14 5588.
19. W. Baratta G. Chelucci S. Magnolia K. Siega P. Rigo Chem.–Eur. J. 2009 15 726.
20. For reviews, see: R. C. van der Drift E. Bouwman E. Drent J. Organomet. Chem. 2002 650 1.
21. R. Uma C. Crévisy R. Grée Chem. Rev. 2003 103 27.
22. V. Cadierno P. Crochet J. Gimeno Synlett 2008 1105.
23. For recent examples of highly efficient catalysts, see: M. Ito S. Kitahara T. Ikariya J. Am. Chem. Soc. 2005 127 6172.
24. B. Martín-Matute K. Bogár M. Edin F. B. Kaynak J.-E. Bäckvall Chem.–Eur. J. 2005 11 5832.
25. P. Crochet M. A. Fernández-Zúmel J. Gimeno M. Scheele Organometallics 2006 25 4846.
26. L. Mantilli C. Mazet Tetrahedron Lett. 2009 50 4141.
27. L. Mantilli D. Gérard S. Torche C. Besnard C. Mazet Angew. Chem., Int. Ed. 2009 48 5143.
28. Examples of metal-catalyzed hydrogenation of allylic alcohols can be found in: H. Takaya T. Ohta S. Inoue M. Katimura R. Noyori Org. Synth. 1995 72 74.
29. Y. Sun C. Le Blond J. Wang D. G. Blackmond J. Laquidara J. R. Sowa Jr J. Am. Chem. Soc. 1995 117 12647.
30. D. G. Blackmond A. Lightfoot A. Pfaltz T. Rosner P. Schnider N. Zimmermann Chirality 2000 12 442.
31. Z. Yang M. Ebihara T. Kawamura J. Mol. Catal. A: Chem. 2000 158 509.
32. N. Makihara S. Ogo Y. Watanabe Organometallics 2001 20 497.
33. S. Nanchen A. Pfaltz Helv. Chim. Acta 2006 89 1559.
34. Q. Chen F.-L. Qing Tetrahedron 2007 63 11965.
35. See, for example: J. C. Li and T. H. Chan, Organic Reactions in Aqueous Media, John Willey & Sons, New York, 1997.
36. A. S. Matlack, Introduction to Green Chemistry, Marcel Dekker, New York, 2001.
37. U. M. Lindström Chem. Rev. 2002 102 2751.
38. M. Lancaster, Green Chemistry: An Introductory Text, RSC, Cambridge, 2002.
39. C.-J. Li Chem. Rev. 2005 105 3095.
40. C.-J. Li L. Chen Chem. Soc. Rev. 2006 35 68.
41. Organic Reactions in Water: Principles, Strategies and Applications, ed. U. M. Lindström, Blackwell, Oxford, 2007.
42. S. Y. Tang R. A. Bourne R. L. Smith M. Poliakoff Green Chem. 2008 10 268.
43. Examples of redox-isomerizations of allylic alcohols in aqueous media can be found in: D. V. McGrath R. H. Grubbs J. W. Ziller J. Am. Chem. Soc. 1991 113 3611.
44. T. Karlen A. Ludi Helv. Chim. Acta 1992 75 1604.
45. D. V. McGrath R. H. Grubbs Organometallics 1994 13 224.
46. H. Schummann V. Ravindar L. Meltser W. Baidossi Y. Sasson J. Blum J. Mol. Catal. A: Chem. 1997 118 55.
47. V. Cadierno P. Crochet S. E. García-Garrido J. Gimeno Dalton Trans. 2004 3635.
48. V. Cadierno S. E. García-Garrido J. Gimeno Chem. Commun. 2004 232.
49. V. Cadierno S. E. García-Garrido J. Gimeno A. Varela-Álvarez J. A. Sordo J. Am. Chem. Soc. 2006 128 1360.
50. V. Cadierno P. Crochet S. E. García-Garrido J. Gimeno Curr. Org. Chem. 2006 10 165.
51. A. E. Díaz-Álvarez P. Crochet M. Zablocka C. Duhayon V. Cadierno J. Gimeno J. P. Majoral Adv. Synth. Catal. 2006 348 1671.
52. P. Crochet J. Díez M. A. Fernández-Zúmel J. Gimeno Adv. Synth. Catal. 2006 348 93.
53. M. Fekete F. Joó Catal. Commun. 2006 7 783.
54. T. Campos-Malpartida M. Fekete F. Joó A. Kathó A. Romerosa M. Saoud W. Wojtków J. Organomet. Chem. 2008 693 468.
55. B. Lastra-Barreira J. Díez P. Crochet Green Chem. 2009 11 1681 10.1039/b914789f.
56. Examples of TH reactions in aqueous media can be found in: F. Joó A. Bényei J. Organomet. Chem. 1989 363 C19.
57. D. J. Darensbourg F. Joó M. Kannisto A. Kathó J. H. Reibenspies Organometallics 1992 11 1990.
58. D. J. Darensbourg F. Joó M. Kannisto A. Kathó J. H. Reibenspies D. J. Daigle Inorg. Chem. 1994 33 200.
59. H. Y. Rhyoo R.-J. Park Y.-K. Chung Chem. Commun. 2001 2064.
60. S. Ogo T. Abura Y. Watanabe Organometallics 2002 21 2964.
61. F. Joó Acc. Chem. Res. 2002 35 738.
62. Y. Ma H. Liu L. Chen X. Cui J. Zhu J. Deng Organometallics 2003 22 2103.
63. P. N. Liu J. G. Deng Y. Q. Tu S. H. Wang Chem. Commun. 2004 2070.
64. X. Wu X. Li F. King J. Xiao Angew. Chem., Int. Ed. 2005 44 3407.
65. J. Mao B. Wan F. Wu S. Lu Tetrahedron Lett. 2005 46 7341.
66. D. S. Matharu D. J. Morris G. J. Clarkson M. Wills Chem. Commun. 2006 3232.
67. X. Wu J. Xiao Chem. Commun. 2007 2449.
68. X. Wu X. Li A. Zanotti-Gerosa A. Pettman J. Liu A. J. Mills J. Xiao Chem.–Eur. J. 2008 14 2209.
69. C. Wang X. Wu J. Xiao Chem.–Asian J. 2008 3 1750.
70. Part of this work has been preliminary communicated: V. Cadierno J. Francos J. Gimeno N. Nebra Chem. Commun. 2007 2536.
71. 2) can also act as efficient heterogeneous catalysts for this transformation: J. W. Kim T. Koike M. Kotani K. Yamaguchi N. Mizuno Chem.–Eur. J. 2008 14 4104.
72. K. Yamaguchi T. Koike J. W. Kim Y. Ogasawara N. Mizuno Chem.–Eur. J. 2008 14 11480.
73. Both individual steps, i.e. the allylic alcohol isomerization and the TH of the carbonyl intermediate, require the use of a base as co-catalyst to promote the formation of the active metal-hydride species. As expected, very low conversions (0–15%) of the substrate were observed in the absence of base.
74. tBu) and [Ru] : [base] ratios (from 1 : 1 to 1 : 24) were checked without success.
75. −1. See references 10f–g.
76. 2] in redox isomerization processes (see ref. 16).
77. A. Inoue K. Kitagawa H. Shinokubo K. Oshima J. Org. Chem. 2001 66 4333.
78. Coordination of the carbon–carbon double bond is a key step in the different catalytic cycles proposed for the metal-catalyzed redox isomerization of allylic alcohols. For mechanistic discussions see ref. 6.
79. See, for example: U. K. Singh M. N. Sysak M. A. Vannice J. Catal. 2000 191 181.
80. F. Zaccheria N. Ravasio A. Fusi M. Rodondi R. Psaro Adv. Synth. Catal. 2005 347 1267.
81. P. Mäki-Arvela N. Kumar A. Nasir T. Salmi D. Y. Murzin Ind. Eng. Chem. Res. 2005 44 9376.
82. F. Goettmann P. Le Floch C. Sanchez Chem. Commun. 2006 2036.
83. P. Claus F. Raif S. Cavet S. Demirel-Gülen J. Radnik M. Schreyer T. Fässler Catal. Commun. 2006 7 618.
84. J. C. Serrano-Ruiz A. Sepúlveda-Escribano F. Rodríguez-Reinoso D. Duprez J. Mol. Catal. A: Chem. 2007 268 227.
85. M. D. Bhor A. G. Panda S. R. Jagtap B. M. Bhanage Catal. Lett. 2008 124 157.
86. M. Ueno T. Suzuki T. Naito H. Oyamada S. Kobayashi Chem. Commun. 2008 1647.
87. V. Cadierno J. Francos J. Gimeno Chem.–Eur. J. 2008 14 6601.
88. In spite of the insolubility of complex 1 in water, the reduction process proceeded efficiently. A close examination of the reaction mixture showed that it was an emulsion rather than a homogeneous solution, the catalytic reaction probably taking place at the interface.
89. 2O conditions. See ref. 11.
90. Complexes 1 and 2 are commercialized by TCI Laboratory Chemicals and Strem Chemicals Inc., respectively.
91. We note that a related Ru-catalyzed isomerization/hydrogenation tandem process in aqueous media has been reported:.
92. P. Csabai F. Joó Organometallics 2004 23 5640.
93. M. A. Bennett A. K. Smith J. Chem. Soc., Dalton Trans. 1974 233.
94. M. A. Bennett T. N. Huang T. W. Matheson A. K. Smith Inorg. Synth. 1982 21 74.
95. J. K. Nicholson B. L. Shaw J. Chem. Soc. A 1966 807.
96. L. Porri M. C. Gallazzi A. Colombo G. Allegra Tetrahedron Lett. 1965 6 4187.
97. A. Salzer A. Bauer S. Geyser F. Podewils Inorg. Synth. 2004 34 59.
98. P. S. Hallman T. A. Stephenson G. Wilkinson Inorg. Synth. 1970 12 237.
99. J. Powell B. L. Shaw J. Chem. Soc. A 1968 159.
100. M. O. Albers T. V. Ashworth H. E. Oosthuizen E. Singleton Inorg. Synth. 1989 26 68.
101. I. P. Evans A. Spencer G. Wilkinson J. Chem. Soc., Dalton Trans. 1973 204.
102. M. I. Bruce C. Hameister A. G. Swincer R. C. Wallis Inorg. Synth. 1982 21 78.
103. M. I. Bruce C. Hameister A. G. Swincer R. C. Wallis Inorg. Synth. 1990 28 270.
104. L. A. Oro M. A. Ciriano M. Campo C. Foces-Foces F. H. Cano J. Organomet. Chem. 1985 289 117.
105. G. Giordano R. H. Crabtree Inorg. Synth. 1979 19 218.
106. G. Giordano R. H. Crabtree Inorg. Synth. 1990 28 88.
107. E. W. Abel M. A. Bennett G. Wilkinson J. Chem. Soc. 1959 3178.
108. A. Van Der Ent A. L. Onderdelinden Inorg. Synth. 1973 14 92.
109. J. L. Herde J. C. Lambert C. V. Senoff Inorg. Synth. 1974 15 18.
110. M. K. Gurjar P. Yakambram Tetrahedron Lett. 2001 42 3633.
111. S. Laabs W. Münch J. W. Bats U. Nubbemeyer Tetrahedron 2002 58 1317.
112. B. Schmidt J. Org. Chem. 2004 69 7672.
113. D. M. Speare S. M. Fleming M. N. Beckett J.-J. Li T. D. H. Bugg Org. Biomol. Chem. 2004 2 2942.
114. N. Marion R. Gealageas S. P. Nolan Org. Lett. 2007 9 2653.
115. U. M. Krishna G. S. C. Srikanth G. K. Trivedi Tetrahedron Lett. 2003 44 8227.
116. G. Dyker D. Kadzimirsz G. Henkel Tetrahedron Lett. 2003 44 7905.
117. T. N. Grant F. G. West J. Am. Chem. Soc. 2006 128 9348.
118. B. D. Stevens C. J. Bungard S. G. Nelson J. Org. Chem. 2006 71 6397.
119. N. S. Nudelman G. V. García J. Org. Chem. 2001 66 1387.