Novel α-pinene-derived mono- and bisphosphinite ligands: Synthesis and application in catalytic hydrogenation

Inorganica Chimica Acta

Volumn 374, Issue 1, 2011, Pages 94-103

  Hobuß, Dennis ^a   Hasenjäger, Jens ^b   Driessen Hölscher, Birgit ^b   Baro, Angelika ^a   Axenov, Kirill V ^a   Laschat, Sabine ^a   Frey, Wolfgang ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF PADERBORN   (Germany)

Author keywords

Catalytic hydrogenation; Phosphinite ligands; Rhodium; Terpenes

Indexed keywords

CATALYST ACTIVITY; CHELATION; HYDROGENATION; MONOTERPENES; OLEFINS; PRODUCTIVITY; RHODIUM; TERPENES;

CATALYTIC HYDROGENATION; DIMETHYL ITACONATE; ELEVATED TEMPERATURE; HYDROGENATION CATALYST; HYDROGENATION REACTIONS; INCREASED PRODUCTIVITY; PHOSPHINITES; REACTION TEMPERATURE;

LIGANDS;

EID: 79960565049     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2011.01.020     Document Type: Article

References (92)

1. J.A. Osborn, F.H. Jardine, J.F. Young, and G. Wilkinson J. Chem. Soc. A: Inorg. Phys. Theor. 1966 1711
2. A. Pfalz, S. Bell, in: J.G. de Vries, C.J. Elsevier (Eds.), The Handbook of Homogeneous Hydrogenation, Wiley, Weinheim, 2008, pp. 1049-1072 (and references therein).
3. J.R. Shapley, R.R. Schrock, and J.A. Osborn J. Am. Chem. Soc. 91 1969 2816
4. R.R. Schrock, and J.A. Osborn J. Am. Chem. Soc. 93 1971 2397
5. R.R. Schrock, and J.A. Osborn J. Am. Chem. Soc. 98 1976 2134
6. Review: G. Erre, S. Enthaler, K. Junge, S. Gladiali, and M. Beller Coord. Chem. Rev. 252 2008 471 (and references therein)
7. T.P. Dang, and H.B. Kagan J. Chem. Soc., Chem. Commun. 1971 481
8. H.B. Kagan, and T.P. Dang J. Am. Chem. Soc. 94 1972 6429
9. M.T. Reetz Angew. Chem., Int. Ed. 47 2008 2556 (and references therein)
10. K. Tani, T. Yamagata, S. Akutagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori, and S. Otsuka J. Am. Chem. Soc. 106 1984 5208
11. K. Tani, T. Yamagata, Y. Tatsuno, Y. Yamagata, K. Tomita, S. Akutagawa, H. Kumobayashi, and S. Otsuka Angew. Chem., Int. Ed. Engl. 24 1985 217
12. Review: H. Shimizu, I. Nagasaki, K. Matsumura, N. Sayo, and T. Saito Acc. Chem. Res. 40 2007 1385 (and references therein)
13. M.J. Burk J. Am. Chem. Soc. 113 1991 8518
14. M.J. Burk, Y.M. Wang, and J.R. Lee J. Am. Chem. Soc. 118 1996 5142
15. M.J. Burk, C.S. Kalberg, and A. Pizzano J. Am. Chem. Soc. 120 1998 4345
16. M.J. Burk Acc. Chem. Res. 33 2000 363
17. Review: W. Zhang, Y. Chi, and X. Zhang Acc. Chem. Res. 40 2007 1278 (and references therein)
18. A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, and A. Tijani J. Am. Chem. Soc. 116 1994 4062
19. Review: H.-U. Blaser Nachr. Chem. 58 2010 864 (and references therein)
20. A.J. Minnaard, B.L. Feringa, L. Lefort, and J.G. de Vries Acc. Chem. Res. 40 2007 1267 (and references therein)
21. L. Eberhardt, D. Armspach, J. Harrowfield, and D. Matt Chem. Soc. Rev. 37 2008 839 (and references therein)
22. J.F. Teichert, and B.L. Feringa Angew. Chem., Int. Ed. 49 2010 2486 (and references therein)
23. R.H. Grubbs, and R.A. DeVries Tetrahedron Lett. 18 1977 1879
24. J. Bakos, I. Tóth, and L. Markó J. Org. Chem. 46 1981 5427
25. A.S.C. Chan, W. Hu, C.-C. Pai, C.-P. Lau, Y. Jiang, A. Mi, M. Yan, J. Sun, R. Lou, and J. Deng J. Am. Chem. Soc. 119 1997 9570
26. M.T. Reetz, and G. Mehler Angew. Chem., Int. Ed. 39 2000 3889
27. I.D. Kostas, K.A. Vallianatou, J. Holz, and A. Börner Appl. Organomet. Chem. 19 2005 1090
28. C. Darcel, D. Moulin, J.-C. Henry, M. Lagrelette, P. Richard, P.D. Harvey, and S. Jugé Eur. J. Org. Chem. 2007 2078
29. H. Fernández-Pérez, S.M.A. Donald, I.J. Munslow, J. Benet-Buchholz, F. Maseras, and A. Vidal-Ferran Chem. Eur. J. 16 2010 6495 (and references therein)
30. T.H. Johnson, and G. Rangarajan J. Org. Chem. 45 1980 62
31. M.T. Reetz, and T. Neugebauer Angew. Chem., Int. Ed. 38 1999 179
32. E. Guimet, M. Diéguez, A. Ruiz, and C. Claver Tetrahedron: Asymmetry 15 2004 2247
33. T. Minuth, and M.M.K. Boysen Org. Lett. 11 2009 4212
34. Review: M. Diéguez, O. Pmies, and C. Claver Chem. Rev. 104 2004 3189 (and references therein)
35. H. Brunner, W. Zettelmeier, Handbook of Enantioselective Catalysis with Transition Metals, first ed., vol. I and II, VCH, Weinheim, 1993.
36. I. Ojima, Asymmetric Catalysis, VCH, Weinheim, 1993.
37. D. Valentine Jr., K.K. Johnson, W. Priester, R.C. Sun, K. Toth, G. Saucy, J. Org. Chem. 45 (1980) 3698.
38. J. Almena, A. Monsees, T. Riermeier, and R. Kadyrov Chim. Oggi 23 2005 48
39. R. Zalubovskis, E. Hörmann, A. Pfaltz, and C. Moberg ARKIVOC 14 2008 58
40. K.Z. Łczkowski, A. Kmieciak, and A. Kozakiewicz Tetrahedron: Asymmetry 20 2009 1487
41. K.Z. Łczkowski, and A. Baranowska Eur. J. Org. Chem. 2009 4600
42. B. Bogdanović, B. Henc, B. Meister, H. Pauling, and G. Wilke Angew. Chem., Int. Ed. Engl. 11 1972 1023
43. J.D. Morrison, W.F. Masler, and M.K. Neuberg Adv. Catal. 25 1976 81
44. T.H. Johnson, D.K. Pretzer, S. Thomen, V.J.K. Chaffin, and G. Rangarajan J. Org. Chem. 44 1979 1878
45. D.A. Knight, D.J. Cole-Hamilton, and D.C. Cupertino J. Chem. Soc., Dalton Trans. 1990 3051
46. E.U. Zhorov, K.N. Gavrilov, V.A. Pavlov, A.T. Teleshev, L.S. Gorshkova, E.E. Nifantev, and E.I. Klabunovskii Russ. Chem. Bull. 1991 871
47. A. Alexakis, J. Vastra, J. Burton, and P. Mangeney Tetrahedron: Asymmetry 8 1997 3193
48. X. Li, R. Lou, C.-H. Yeung, A.S.C. Chan, and W.K. Wong Tetrahedron: Asymmetry 11 2000 2077
49. I.V. Komarov, M.V. Gorichko, and M.Y. Kornilov Tetrahedron: Asymmetry 8 1997 435
50. I.V. Komarov, A. Monsees, R. Kadyrov, C. Fischer, U. Schmidt, and A. Börner Tetrahedron: Asymmetry 13 2002 1615
51. I.V. Komarov, A. Monsees, A. Spannenberg, W. Baumann, U. Schmidt, C. Fischer, and A. Börner Eur. J. Org. Chem. 2003 138
52. R. Kadyrov, I.Z. Ilaldinov, J. Almena, A. Monsees, and T.H. Riermeier Tetrahedron Lett. 46 2005 7397 (and references therein)
53. A. Lledó, J. Sol, X. Verdaguer, A. Riera, and M.A. Maestro Adv. Synth. Catal. 349 2007 2121
54. T. Sell, S. Laschat, I. Dix, and P.G. Jones Eur. J. Org. Chem. 2000 4119
55. A. Monsees, and S. Laschat Synlett 2002 1011
56. F. Langer, and P. Knochel Tetrahedron Lett. 36 1995 4591
57. A. Longeau, F. Langer, and P. Knochel Tetrahedron Lett. 37 1996 2209
58. A. Gavryushin, K. Polborn, and P. Knochel Tetrahedron: Asymmetry 15 2004 2279
59. E.J. Bergner, and G. Helmchen Eur. J. Org. Chem. 2000 419
60. K.W. Kottsieper, U. Kühner, and O. Stelzer Tetrahedron: Asymmetry 12 2001 1159
61. X. Meng, X. Li, and D. Xu Tetrahedron: Asymmetry 20 2009 1402
62. C.M. Binder, A. Bautista, M. Zaidlewicz, M.P. Krzemiński, A. Oliver, and B. Singaram J. Org. Chem. 74 2009 2337
63. D. Wei, M. Tang, J. Zhao, L. Sun, W. Zhang, C. Zhao, S. Zhang, and H. Wang Tetrahedron: Asymmetry 20 2009 1020
64. D. Hobuß, C. Thöne, S. Laschat, and A. Baro Synthesis 2003 2053
65. J.M. Brown, in: E.N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, vol. 1, Springer Verlag, New York, 1999, pp. 1-62.
66. K. Rossen Angew. Chem., Int. Ed. 40 2001 4611
67. W.S. Knowles Angew. Chem., Int. Ed. 41 2002 1998
68. R. Noyori Angew. Chem., Int. Ed. 41 2002 2008
69. W.S. Knowles, and R. Noyori Acc. Chem. Res. 40 2007 1238
70. I.D. Gridnev, and T. Imamoto Acc. Chem. Res. 37 2004 633
71. I.D. Gridnev, and T. Imamoto Chem. Commun. 2009 7447
72. H. Shimizu, I. Nagasaki, K. Matsumura, N. Sayo, and T. Saito Acc. Chem. Res. 40 2007 1385
73. I.V. Komarov, and A. Börner Angew. Chem., Int. Ed. 40 2001 1197
74. V.I. Tararov, R. Kadyrov, T.H. Riermeier, J. Holz, and A. Börner Tetrahedron Lett. 41 2000 2351
75. G. Zhu, P. Cao, Q. Jiang, and X. Zhang J. Am. Chem. Soc. 119 1997 1799
76. H. Firouzabadi, N. Iranpoor, G. Hajipoor, and J. Toofan Synth. Commun. 14 1984 1033
77. N. Iranpoor, and F.S. Zardaloo Synth. Commun. 24 1994 1959
78. M.K. Lajunen, T. Maunula, and A.M.P. Koskinen Tetrahedron 56 2000 8167
79. B.A. Allal, L.E. Firdoussi, S. Allaoud, A. Karim, Y. Castanet, and A. Mortreux J. Mol. Catal. A: Chem. 200 2003 177
80. R.G. Carlson, and J.K. Pierce J. Org. Chem. 36 1971 2319
81. Crystallographic data (excluding structure factors) for the structures included in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. C≡CDC 791978 and 791979. Copies of the data can be obtained free of charge on application to C≡CDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (internet) +44(1223)336-033, E-mail: deposit@ccdc.cam.ac.uk.
82. M. Ohff, J. Holz, M. Quirmbach, and A. Börner Synthesis 1998 1391
83. O. Huttenloch, J. Spieler, and H. Waldmann Chem. Eur. J. 7 2001 671
84. A. Arbuzov, and K. Nikonorov Rus. J. Gen. Chem. 18 1948 2008
85. Knochel has recently utilized the Arbuzov rearrangement for a transformation of allylphosphinites to allylphosphine oxides. For details see Ref. [58].
86. P.-Y. Renard, P. Vayron, E. Leclerc, A. Valleix, and C. Mioskowski Angew. Chem., Int. Ed. 42 2003 2389
87. M. van der Berg, A.J. Minnaard, R.M. Haak, M. Leeman, E.P. Schudde, A. Meetsma, B.L. Feringa, A.H.M. de Vries, C.E.P. Maljaars, C.E. Willans, D. Hyett, J.A.F. Boogers, H.J.W. Henderickx, and J.G. de Vries Adv. Synth. Catal. 345 2003 308
88. M.T. Reetz, and A. Gosberg Tetrahedron: Asymmetry 10 1999 2129
89. For example, the methoxy substituent at the (-)-α-pinane core could be converted into a hydroxyl group, which is known to improve selectivity of a Rh hydrogenation catalyst. See Refs. [90-92].
90. A. Börner, A. Kless, R. Kempe, D. Heller, J. Holz, and W. Baumann Chem. Ber. 128 1995 767
91. S. Borns, R. Kadyrov, D. Heller, W. Baumann, A. Spannenberg, R. Kempe, J. Holz, and A. Börner Eur. J. Inorg. Chem. 1998 1291
92. A. Börner Eur. J. Inorg. Chem. 2001 327