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The Influence of Substituents in Diphosphine Ligands on the Hydrogenation Activity and Selectivity of the Corresponding Rhodium Complexes as Exemplified by ButiPhane

Dr. Christian Fischer¹,
Dr. Stefan Schulz¹,
Dr. Hans-Joachim Drexler¹,
Carmen Selle¹,
Dr. Matthias Lotz²,
Dr. Mathias Sawall³,
Prof. Dr. Klaus Neymeyr³,
Prof. Dr. Detlef Heller^1,*

Article first published online: 17 NOV 2011

DOI: 10.1002/cctc.201100277

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ChemCatChem

Volume 4, Issue 1, pages 81–88, January 2, 2012

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How to Cite

Fischer, C., Schulz, S., Drexler, H.-J., Selle, C., Lotz, M., Sawall, M., Neymeyr, K. and Heller, D. (2012), The Influence of Substituents in Diphosphine Ligands on the Hydrogenation Activity and Selectivity of the Corresponding Rhodium Complexes as Exemplified by ButiPhane. ChemCatChem, 4: 81–88. doi: 10.1002/cctc.201100277

Author Information

¹
Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29 A, 18059 Rostock (Germany), Fax: (+49) 381-12815000
²
Solvias AG, Klybeckstr. 191, Postfach, CH-4002 Basel (Switzerland)
³
Universität Rostock, Institut für Mathematik, Ulmenstr. 69, 18057 Rostock (Germany)

Email: Prof. Dr. Detlef Heller (detlef.heller@catalysis.de)

^*Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29 A, 18059 Rostock (Germany), Fax: (+49) 381-12815000

Publication History

Issue published online: 27 DEC 2011
Article first published online: 17 NOV 2011
Manuscript Received: 15 AUG 2011

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1
1a
M. J. Burk, J. E. Feaster, R. L. Harlow, Organometallics 1990, 9, 2653–2655;
1b
M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266–6267;
1c
M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, J. Am. Chem. Soc. 1993, 115, 10125–10138;
1d
M. J. Burk, M. F. Gross, J. P. Martinez, J. Am. Chem. Soc. 1995, 117, 9375–9376;
1e
M. J. Burk, Y. M. Wang, J. R. Lee, J. Am. Chem. Soc. 1996, 118, 5142–5143;
1f
M. J. Burk, J. G. Allen, W. F. Kiesmann, J. Am. Chem. Soc. 1998, 120, 657–663;
1g
M. J. Burk, Acc. Chem. Res. 2000, 33, 363–372.
2
2a
T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691–1693.
3
J. Holz, M. Quirmbach, U. Schmidt, D. Heller, R. Stürmer, A. Börner, J. Org. Chem. 1998, 63, 8031–8034.
4
4a
J. Holz, D. Heller, R. Stürmer, A. Börner, Tetrahedron Lett. 1999, 40, 7059–7062;
4b
J. Holz, R. Stürmer, U. Schmidt, H.-J. Drexler, D. Heller, H.-P. Krimmer, A. Börner, Eur. J. Org. Chem. 2001, 4615–4624.
Direct Link:
5
5a
J. Holz, A. Monsees, H. Jiao, J. You, I. V. Komarov, C. Fischer, K.-H. Drauz, A. Börner, J. Org. Chem. 2003, 68, 1701–1707;
5b
J. Almena, A. Monsees, R. Kadyrov, T. H. Riermeier, B. Gotov, J. Holz, A. Börner, Adv. Synth. Catal. 2004, 346, 1263–1266;
Direct Link:
5c
J. Holz, O. Zayas, H. Jiao, W. Baumann, A. Spannenberg, A. Monsees, T. H. Riermeier, J. Almena, R. Kadyrov, A. Börner, Chem. Eur. J. 2006, 12, 5001–5013.
Direct Link:
6
T. Benincori, T. Pilati, S. Rizzo, F. Sannicolo, M. J. Burk, L. de Ferra, E. Ullucci, O. Piccolo, J. Org. Chem. 2005, 70, 5436–5441.
7
U. Berens, U. Englert, S. Geyser, J. Runsink, A. Salzer, Eur. J. Org. Chem. 2006, 2006, 2100–2109.
Direct Link:
8
P. Feiertag, M. Albert, U. Nettekoven, F. Spindler, Org. Lett. 2006, 8, 4133–4135.
9
Due to isobaric conditions, the determined pseudo rate constants still contain the hydrogen concentration in solution, which is proportional to the overall pressure above the solution under consideration of the solvent vapor pressure: k'_2diolefin=k_2diolefin[H₂].
10
A. Preetz, H.-J. Drexler, C. Fischer, Z. Dai, A. Börner, W. Baumann, A. Spannenberg, R. Thede, D. Heller, Chem. Eur. J. 2008, 14, 1445–1451.
Direct Link:
11
Standard conditions: 0.01 mmol rhodium complex and 1.0 mmol prochiral olefin in 15.0 mL MeOH at 25.0 °C and 1 bar total pressure.
12
Hydrogen consumption rates cannot register greater than 12 mL min⁻¹ without influence of diffusion for the used hydrogenation equipment.
13
The purity of commercially available diolefin precatalysts, the licensing rights of which are held by Solvias AG, is higher than 95 % as determined by using ³¹P NMR spectroscopy. When necessary, the diolefin complexes can be further purified through simple recrystallization in methanol or dichloromethane/diethyl ether mixture, respectively.
14
H.-J. Drexler, J.-T. Sun, D. Heller, U. Berens, M. Kesselgruber, Z. Kristallogr. New Cryst. Struct. 2005, 220, 435–436.
- CAS
15
I. Bonnaventure, A. B. Charette, J. Org. Chem. 2008, 73, 6330–6340.
16
16a
Catalyst Inhibition and Deactivation in Homogeneous Hydrogenation, D. Heller, A. H. M. de Vries, J. G. de Vries in Handbook of Homogeneous Hydrogenation (Eds.: H. G. de Vries, C. Elsevier), Wiley-VCH, Weinheim, 2007, chap. 44, pp. 1483–1516;
16b
H.-J. Drexler, J. You, S. Zhang, C. Fischer, W. Baumann, A. Spannenberg, D. Heller, Org. Process Res. Dev. 2003, 7, 355–361;
16c
D. Heller, H.-J. Drexler, J. You, W. Baumann, K. Drauz, H.-P. Krimmer, A. Börner, Chem. Eur. J. 2002, 8, 5196–5202;
Direct Link:
16d
D. Heller, J. Holz, H.-J. Drexler, J. Lang, K. Drauz, H.-P. Krimmer, A. Börner, J. Org. Chem. 2001, 66, 6816–6817;
16e
H.-J. Drexler, W. Baumann, A. Spannenberg, C. Fischer, D. Heller, J. Organomet. Chem. 2001, 621, 89–102.
17
17a
L. Greiner, M. B. Ternbach, Adv. Synth. Catal. 2004, 346, 1392–1396;
Direct Link:
17b
C. J. Cobley, I. C. Lennon, R. McCague, J. A. Ramsden, A. Zanotti-Gerosa, Tetrahedron Lett. 2001, 42, 7481–7483;
17c
D. G. Blackmond, T. Rosner, T. Neugebauer, M. T. Reetz, Angew. Chem. 1999, 111, 2333–2335;
Direct Link:
Angew. Chem. Int. Ed. 1999, 38, 2196–2199;
Direct Link:
- Abstract
- PDF(108K)
17d
U. Nagel, T. Krink, Angew. Chem. 1993, 105, 1099–1101;
Direct Link:
Angew. Chem. Int. Ed. Engl. 1993, 32, 1052–1054.
Direct Link:
18
C. R. Landis, J. Halpern, J. Am. Chem. Soc. 1987, 109, 1746–1754.
19
H. Mauser in Formale Kinetik, Bertelsmann Universitätsverlag, Düsseldorf, 1974.
20
Specfit is a tool for fitting spectroscopic data (emission lines, absorption lines, and continua to one-dimensional spectra):
20a
H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 95–101;
20b
H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 257–264;
- PubMed,
- CAS
20c
H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 1133–1139;
20d
H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1986, 33, 943–951.
21
E. R. Malinowski in Factor analysis in chemistry, Wiley-VCH, New York, 2002.
22
22a
M. Garland, Catal. Today 2010, 155, 266–270;
22b
E. Widjaja, C. Li, M. Garland, J. Catal. 2004, 223, 278–289;
22c
C. Li, L. Guo, M. Garland, Organometallics 2004, 23, 2201–2204;
22d
C. Li, E. Wadjaja, M. Garland, J. Am. Chem. Soc. 2003, 125, 5540–5548;
22e
C. Li, E. Widjaja, M. Garland, J. Catal. 2003, 213, 126–134;
22f
E. Widjaja, C. Z. Li, W. Chew, M. Garland, Anal. Chem. 2003, 75, 4499–4507;
22g
E. Widjaja, C. Li, M. Garland, Organometallics 2002, 21, 1991–1997;
22h
W. Chew, E. Widjaja, M. Garland, Organometallics 2002, 21, 1982–1990;
22i
C. Li, E. Widjaja, W. Chew, M. Garland, Angew. Chem. 2002, 114, 3939–3943;
Direct Link:
Angew. Chem. Int. Ed. 2002, 41, 3785–3789;
Direct Link:
22j
Y. Zeng, M. Garland, Anal. Chim. Acta 1998, 359, 303–310.
23
K. Neymeyr, M. Sawall, D. Hess, J. Chemom. 2010, 24, 67–74.
- CAS
24
D. Heller, R. Thede, D. Haberland, J. Mol. Catal. A 1997, 115, 273–281.
25
Kinetics of homogeneous hydrogenations: measurement and interpretation, H.-J. Drexler, A. Preetz, T. Schmidt, D. Heller in Handbook of Homogeneous Hydrogenation (Eds.: H. G. de Vries, C. Elsevier), Wiley-VCH, Weinheim, 2007, chap. 10, pp. 257–293.
26
A. Preetz, H.-J. Drexler, S. Schulz, D. Heller, Tetrahedron: Asymmetry 2010, 21, 1226–1231.
27
G. Zhu, Z. Chen, X. Zhang, J. Org. Chem. 1999, 64, 6907–6910.
28
J. You, H.-J. Drexler, S. Zhang, C. Fischer, D. Heller, Angew. Chem. 2003, 115, 942–945;
Direct Link:
Angew. Chem. Int. Ed. 2003, 42, 913–916.
Direct Link:
29
29a
A. S. C. Chan, J. J. Pluth, J. Halpern, J. Am. Chem. Soc. 1980, 102, 5952–5954;
29b
B. McCulloch, J. Halpern, M. R. Thomas, C. R. Landis, Organometallics 1990, 9, 1392–1395;
29c
T. Schmidt, W. Baumann, H.-J. Drexler, A. Arrieta, D. Heller, H. Buschmann, Organometallics 2005, 24, 3842–3848;
29d
A. Preetz, W. Baumann, C. Fischer, H.-J. Drexler, T. Schmidt, R. Thede, D. Heller, Organometallics 2009, 28, 3673–3677.
30
30a
D. Evans, F. E. Michael, J. S. Tedrow, K. R. Campos, J. Am. Chem. Soc. 2003, 125, 3534–3543;
30b
H.-J. Drexler, W. Baumann, T. Schmidt, S. Zhang, A. Sun, A. Spannenberg, C. Fischer, H. Buschmann, D. Heller, Angew. Chem. 2005, 117, 1208–1212;
Direct Link:
Angew. Chem. Int. Ed. 2005, 44, 1184–1188.
Direct Link:
31
31a
J. Halpern, D. P. Riley, A. S. C. Chan, J. J. Pluth, J. Am. Chem. Soc. 1977, 99, 8055–8057;
31b
C. R. Landis, J. Halpern, Organometallics 1983, 2, 840–842.
32
32a
C. Fischer, T. Berweries, A. Preetz, H.-J. Drexler, W. Baumann, S. Peitz, U. Rosenthal, D. Heller, Catal. Today 2010, 155, 282–288;
32b
H. A. Benesi, J. H. Hildebrand, J. Am. Chem. Soc. 1949, 71, 2703;
32c
G. Scatchard, Ann. N. Y. Acad. Sci. 1949, 51, 660–672.
Direct Link:
33
33a
A. Salzer in Synthetic Methods of Organometallic and Inorganic Chemistry (Ed.: W. A. Herrmann), Georg Thieme Verlag, Stuttgart, 1996, chap. 2, pp. 8—28;
33b
S. Herzog, J. Dehnert, K. Lühder in Technique Of Inorganic Chemistry, Vol. VII (Eds.: H. B. Jonassen, A. Weissberger), Wiley, New York, 1968, chap. 5, pp. 119–149.
34
G. M. Sheldrick, Acta Crystallogr. Sect. A 1997, 64, 112–122.
Direct Link:

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The Influence of Substituents in Diphosphine Ligands on the Hydrogenation Activity and Selectivity of the Corresponding Rhodium Complexes as Exemplified by ButiPhane

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The Influence of Substituents in Diphosphine Ligands on the Hydrogenation Activity and Selectivity of the Corresponding Rhodium Complexes as Exemplified by ButiPhane

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