Unravelling the reaction path of rhodium-monophos-catalysed olefin hydrogenation

Chemistry - A European Journal

Volumn 17, Issue 45, 2011, Pages 12683-12695

  Alberico, Elisabetta ^a   Baumann, Wolfgang ^b   De Vries, Johannes G ^c   Drexler, Hans Joachim ^b   Gladiali, Serafino ^d   Heller, Detlef ^b   Henderickx, Huub J W ^c   Lefort, Laurent ^c  

^a CNR   (Italy)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^c DSM Pharmaceutical Products   (Netherlands)

^d UNIVERSITY OF SASSARI   (Italy)

Author keywords

asymmetric catalysis; dimers; phosphoramidites; reactive intermediates; rhodium

Indexed keywords

ANALOGOUS COMPLEXES; AROMATIC RINGS; ASYMMETRIC CATALYSIS; ASYMMETRIC HYDROGENATION; BIMETALLIC COMPLEXES; BINAPHTHYL; CATALYST PRECURSORS; CATALYTIC CYCLES; DIASTEREOMERIC COMPLEXES; DIMERIC COMPLEXES; DIMETHYLAMINES; METHYL ESTERS; OLEFIN HYDROGENATION; PHOSPHORAMIDITES; REACTION PATHS; REACTIVE INTERMEDIATE; RHODIUM COMPLEXES; SOLVATE COMPLEXES; SPECTROSCOPIC SIGNALS; TOTAL PRESSURE;

AMINO ACIDS; CATALYSIS; CATALYSTS; HYDROGENATION; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; REACTION INTERMEDIATES; RHODIUM;

RHODIUM COMPOUNDS;

ALKENE; ORGANOMETALLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDOUS ACID; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ALKENES; CATALYSIS; HYDROGENATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 80054961249     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101793     Document Type: Article

References (82)

1. Handbook of Homogeneous Hydrogenation, (Eds.:, J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007
2. I. D. Gridnev, T. Imamoto, Chem. Commun. 2009, 7447-7464, and references therein.
3. F. Lagasse, H. B. Kagan, Chem. Pharm. Bull. 2000, 48, 315-324
4. I. V. Komarov, A. Börner, Angew. Chem. 2001, 113, 1237-1240
5. Angew. Chem. Int. Ed. 2001, 40, 1197-1200
6. C. Claver, E. Fernandez, A. Gillon, K. Heslop, D. J. Hyett, A. Martorell, A. G. Orpen, P. G. Pringle, Chem. Commun. 2000, 961-962
7. M. T. Reetz, G. Mehler, Angew. Chem. 2000, 112, 4047-4049
8. Angew. Chem. Int. Ed. 2000, 39, 3889-3890
9. M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 11539-11540.
10. L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, Org. Lett. 2004, 6, 1733-1735
11. J. G. de Vries, L. Lefort, Chem. Eur. J. 2006, 12, 4722-4734
12. C. Jäkel, R. Paciello, Chem. Rev. 2006, 106, 2912-2942.
13. M. T. Reetz, T. Sell, A. Meiswinkel, G. Mehler, Angew. Chem. 2003, 115, 814-817
14. Angew. Chem. Int. Ed. 2003, 42, 790-793
15. D. Peña, A. J. Minnaard, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Org. Biomol. Chem. 2003, 1, 1087-1089.
16. D. Peña, A. J. Minnaard, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Org. Lett. 2003, 5, 475-478.
17. A. J. Minnaard, B. L. Feringa, L. Lefort, J. G. de Vries, Acc. Chem. Res. 2007, 40, 1267-1277, and references therein
18. L. Eberhardt, D. Armspach, J. Harrowfield, D. Matt, Chem. Soc. Rev. 2008, 37, 839-864
19. D. J. Ager, L. Lefort, J. G. de Vries, ACS Symp. Ser. 2009, 1009, 239-250.
20. J. A. F. Boogers, U. Felfer, M. Kotthaus, L. Lefort, G. Steinbauer, A. H. M. de Vries, J. G. de Vries, Org. Process Res. Dev. 2007, 11, 585-591.
21. M. T. Reetz, A. Meiswinkel, G. Mehler, K. Angermund, M. Graf, W. Thiel, R. Mynott, D. G. Blackmond, J. Am. Chem. Soc. 2005, 127, 10305-10313.
22. Y. Fu, X.-X. Guo, S.-F. Zhu, A.-G. Hu, J.-H. Xie, Q.-L. Zhou, J. Org. Chem. 2004, 69, 4648-4655.
23. I. D. Gridnev, C. Fan, P. G. Pringle, Chem. Commun. 2007, 1319-1321.
24. M. van den 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, J. G. de Vries, Adv. Synth. Catal. 2003, 345, 308-323.
25. A. Preetz, C. Fischer, C. Kohrt, H.-J. Drexler, W. Baumann, D. Heller, Organometallics, DOI:.
26. D. A. Evans, F. E. Michael, J. S. Tedrow, K. R. Campos, J. Am. Chem. Soc. 2003, 125, 3534-3543
27. H.-J. Drexler, W. Baumann, T. Schmidt, S. Zhang, A. Sun, A. Spannenberg, C. Fischer, H. Bauschmann, D. Heller, Angew. Chem. 2005, 117, 1208-1212
28. Angew. Chem. Int. Ed. 2005, 44, 1184-1188
29. for a recent discussion of the Major/Minor concept, see:, T. Schmidt, Z. Dai, H.-J. Drexler, M. Hapke, A. Preetz, D. Heller, Chem. Asian J. 2008, 3, 1170-1180.
30. A. S. C. Chan, J. J. Pluth, J. Halpern, J. Am. Chem. Soc. 1980, 102, 5952-5954
31. J. Halpern, Science 1982, 217, 401-407
32. J. Halpern, in Chiral Catalysis, Vol. 5 (Ed.:, J. D. Morrison,), Academic Press, Orlando, 1985, pp. 41-69
33. C. R. Landis, J. Halpern, J. Am. Chem. Soc. 1987, 109, 1746-1754
34. B. McCulloch, J. Halpern, M. R. Thompson, C. R. Landis, Organometallics 1990, 9, 1392-1395
35. T. Schmidt, W. Baumann, H.-J. Drexler, A. Arrieta, D. Heller, H. Buschmann, Organometallics 2005, 24, 3842-3848
36. T. Schmidt, Z. Dai, H.-J. Drexler, W. Baumann, C. Jäger, D. Pfeifer, D. Heller, Chem. Eur. J. 2008, 14, 4469-4471.
37. M. van den Berg, Ph.D. Thesis, University of Groningen (The Netherlands), 2006;.
38. P. Jankowski, C. L. McMullin, I. D. Gridnev, A. G. Orpen, P. P. Pringle, Tetrahedron: Asymmetry 2010, 21, 1206-1209.
39. N. B. Johnson, I. C. Lennon, P. H. Moran, J. A. Ramsden, Acc. Chem. Res. 2007, 40, 1291-1299.
40. R. R. Schrock, J. A. Osborn, Inorg. Chem. 1971, 10, 2397-2407.
41. I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118-136.
42. D. Heller, A. H. M. de Vries, J. G. de Vries, in Handbook of Homogeneous Hydrogenation, Vol. 3 (Eds.:, J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007, pp. 1483-1516.
43. J. M. Ernsting, S. Gaemers, C. J. Elsevier, Magn. Reson. Chem. 2004, 42, 721-736
44. W. von Philipsborn, Chem. Soc. Rev. 1999, 28, 95-105.
45. 103Rh chemical shift of the corresponding complexes:, A. Fabrello, C. Dinoi, L. Perrin, P. Kalck, L. Maron, M. Urrutigoity, O. Dechy-Cabaret, Magn. Reson. Chem. 2010, 48, 848-856.
46. D. Heller, H.-J. Drexler, A. Spannenberg, B. Heller, J. You, W. Baumann, Angew. Chem. 2002, 114, 814-817
47. Angew. Chem. Int. Ed. 2002, 41, 777-780.
48. 6) and phosphorus has been previously described, see, T. Osswald, H. Rüegger, A Mezzetti, Chem. Eur. J. 2010, 16, 1388-1397, and references therein.
49. J. Halpern, D. P. Riley, A. S. C. Chan, J. J. Pluth, J. Am. Chem. Soc. 1977, 99, 8055-8057
50. D. P. Fairlie, B. Bosnich, Organometallics 1988, 7, 936-945
51. D. P. Fairlie, B. Bosnich, Organometallics 1988, 7, 946-954; DIPAMP
52. A. Preetz, W. Baumann, C. Fischer, H.-J. Drexler, T. Schmidt, R. Thede, D. Heller, Organometallics 2009, 28, 3673-3677; CYCPHOS
53. D. P. Riley, J. Organomet. Chem. 1982, 234, 85-97; DIPH
54. D. G. Allen, S. B. Wild, D. L. Wood, Organometallics 1986, 5, 1009-1015; CHIRAPHOS
55. S. H. Bergens, P. Noheda, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1992, 114, 2121-2128
56. R. W. Barnhart, X. Wang, P. Noheda, S. H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335-4346; SKEWPHOS
57. K. Mikami, Y. Yusa, M. Hatano, K. Wakabayashi, K. Aikawa, Chem. Commun. 2004, 98-99; BIPHEP
58. 3
59. P. Marcazzan, M. B. Ezhova, B. O. Patrick, B. R. James, C. R. Chim. 2002, 5, 373-378; Monophosphonite: reference [10].
60. 2Ph upon hydrogenation in a coordinating solvent at room temperature give rise to stable dihydrides that could be isolated and characterised. According to Halpern (Ref. [27a]) the stability of such dihydrides might be ascribed to the fact that, because of the presence of monophosphines, in the dihydride neither hydrogen ligand needs to be trans to a phosphine (assuming a cis disposition of the two hydrogen atoms).
61. J. M. Brown, P. A. Chaloner, P. N. Nicholson, J. Chem. Soc. Chem. Commun. 1978, 646-647
62. J. M. Brown, P. A. Chaloner, A. G. Kent, B. A. Murrer, P. N. Nicholson, D. Parker, P. J. Sidebottom, J. Organomet. Chem. 1981, 216, 263-276; no stable hydrides were detected when using ligand (R)-(o-methoxyphenyl) phenylmethylphosphine, which probably acts as a chelating ligand through the ortho-methoxy group.
63. J. M. Brown, P. A. Chaloner, Tetrahedron Lett. 1978, 19, 1877-1880
64. A. S. C. Chan, J. J. Pluth, J. Halpern, Inorg. Chim. Acta 1979, 37, L477-L479
65. A. S. C. Chan, J. Halpern, J. Am. Chem. Soc. 1980, 102, 838-840
66. J. M. Brown, P. A. Chaloner, J. Am. Chem. Soc. 1980, 102, 3040-3048
67. J. M. Brown, P. A. Chaloner, J. Chem. Soc. Chem. Commun. 1980, 344-346
68. I. Ojima, T. Kogure, N. Yoda, J. Org. Chem. 1980, 45, 4728-4739
69. J. M. Brown, D. Parker, J. Org. Chem. 1982, 47, 2722-2730.
70. H. Bircher, B. R. Bender, W. von Philipsborn, Magn. Reson. Chem. 1993, 31, 293-298
71. J. M. Brown, P. A. Chaloner, G. A. Morris, J. Chem. Soc. Chem. Commun. 1983, 664-666
72. J. M. Brown, P. A. Chaloner, G. A. Morris, J. Chem. Soc. Perkin Trans. 2 1987, 1583-1588
73. J. A. Ramsden, T. D. W. Claridge, J. M. Brown, J. Chem. Soc. Chem. Commun. 1995, 2469-2471
74. R. Kadyrov, T. Freier, D. Heller, M. Michalik, R. Selke, J. Chem. Soc. Chem. Commun. 1995, 1745-1746
75. D. Heller, R. Kadyrov, M. Michalik, T. Freier, U. Schmidt, H. W. Krause, Tetrahedron: Asymmetry 1996, 7, 3025-3035.
76. B. R. Bender, M. Koller, D. Nanz, W. von Philipsborn, J. Am. Chem. Soc. 1993, 115, 5889-5890.
77. I. D. Gridnev, N. Higashi, K. Asakura, T. Imamoto, J. Am. Chem. Soc. 2000, 122, 7183-7194.
78. J. M. Buriak, J. A. Osborn, J. Chem. Soc. Chem. Commun. 1995, 689-690.
79. C. R. Landis, P. Hilfenhaus, S. Feldgus, J. Am. Chem. Soc. 1999, 121, 8741-8754
80. A. L. Sargent, M. B. Hall, M. F. Guest, J. Am. Chem. Soc. 1992, 114, 517-522.
81. G. Giordano, R. H. Crabtree, Inorg. Synth. 1990, 28, 88-90.
82. R. R. Schrock, J. A. Osborn, J. Am. Chem. Soc. 1971, 93, 3089-3091.