Palladium-catalyzed asymmetric phosphination. Scope, mechanism, and origin of enantioselectivity

Journal of the American Chemical Society

Volumn 129, Issue 21, 2007, Pages 6847-6858

  Blank, Natalia F ^a   Moncarz, Jillian R ^a   Brunker, Tim J ^a   Scriban, Corina ^a   Anderson, Brian J ^a   Amir, Omar ^a   Glueck, David S ^a   Zakharov, Lev N ^b   Golen, James A ^b   Incarvito, Christopher D ^c   Rheingold, Arnold L ^b,c  

^a Dartmouth College   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; STOICHIOMETRY; SUBSTITUTION REACTIONS;

ARYL IODIDES; CATALYST PRECURSORS; DIPHOSPHINES; INTERMEDIATE DIASTEREOMERS;

AROMATIC COMPOUNDS;

LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; STILBENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHIRALITY; CRYSTALLOGRAPHY; DECOMPOSITION; ENANTIOSELECTIVITY; OXIDATION; PHOSPHINATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY;

EID: 34249803212     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja070225a     Document Type: Article

References (77)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994.
2. (b) Blaser, H.-U., Schmidt, E., Eds. Asymmetric Catalysis on Industrial Scale. Challenges, Approaches, and Solutions; Wiley-VCH: Weinheim, 2004.
3. (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411.
4. (b) Kagan, H. B.; Sasaki, M. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley and Sons: Chichester, U.K., 1990; Vol. 1, pp 51-102.
5. (c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3070.
6. (a) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
7. (b) Hoge, G. J. Am. Chem. Soc. 2003, 125, 10219-10227.
8. (c) Shimizu, H.; Saito, T.; Kumobayashi, H. Adv. Synth. Catal. 2003, 345, 185-189.
9. (d) Marinetti, A.; Genet, J.-P. C. R. Chimie 2003, 6, 507-514.
10. (a) Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950-953.
11. (b) Douglass, M. R.; Ogasawara, M.; Hong, S.; Metz, M. V.; Marks, T. J. Organometallics 2002, 21, 283-292.
12. (c) Sadow, A. D.; Haller, I.; Fadini, L.; Togni, A. J. Am. Chem. Soc. 2004, 126, 14704-14705.
13. (d) Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012-17024.
14. (e) Scriban, C.; Kovacik, I.; Glueck, D. S. Organometallics 2005, 24, 4871-4874.
15. (f) Kovacik, I.; Scriban, C.; Glueck, D. S. Organometallics 2006, 25, 536-539.
16. (g) Scriban, C.; Glueck, D. S.; Zakharov, L. N.; Kassel, W. S.; DiPasquale, A. G.; Golen, J. A.; Rheingold, A. L. Organometallics 2006, 25, 5757-5767.
17. For related reactions involving metal-catalyzed enantioselective addition of P-H bonds to unsaturated substrates, see: (h) Shulyupin, M. O.; Franciu, G.; Beletskaya, I. P.; Leitner, W. Adv. Synth. Catal. 2005, 347, 667-672.
18. (i) Xu, Q.; Han, L.-B. Org. Lett. 2006, 8, 2099-2101.
19. (j) Join, B.; Mimeau, D.; Delacroix, O.; Gaumont, A.-C. Chem. Commun. 2006, 3249-3251.
20. (a) Scriban, C.; Glueck, D. S. J. Am. Chem. Soc. 2006, 128, 2788-2789.
21. (b) Chan, V. S.; Stewart, I. C.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 2786-2787.
22. (a) Moncarz, J. R.; Laritcheva, N. F.; Glueck, D. S. J. Am. Chem. Soc. 2002, 124, 13356-13357.
23. (b) Moncarz, J. R.; Brunker, T. J.; Jewett, J. C.; Orchowski, M.; Glueck, D. S.; Sommer, R. D.; Lam, K.-C.; Incarvito, C. D.; Concolino, T. E.; Ceccarelli, C.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2003, 22, 3205-3221.
24. (c) Korff, C.; Helmchen, G. Chem. Commun. 2004, 530-531.
25. (d) Pican, S.; Gaumont, A.-C. Chem. Commun. 2005, 2393-2395.
26. Drago, D.; Pregosin, P. S. Organometallics 2002, 21, 1208-1215.
27. Brauer, D. J.; Bitterer, F.; Dorrenbach, F.; Hessler, G.; Stelzer, O.; Kruger, C.; Lutz, F. Z. Naturforsch. B 1996, 51, 1183-1196.
28. Brunker, T. J.; Blank, N. F.; Moncarz, J. R.; Scriban, C.; Anderson, B. J.; Glueck, D. S.; Zakharov, L. N.; Golen, J. A.; Sommer, R. D.; Incarvito, C. D.; Rheingold, A. L. Organometallics 2005, 24, 2730-2746.
29. For other examples of reversal of enantioselectivity in asymmetric catalysis, see: (a) Evans, D. A.; Johnson, J. S.; Burgey, C. S.; Campos, K. R. Tetrahedron Lett. 1999, 40, 2879-2882.
30. (b) Sibi, M. P.; Liu, M. Curr. Org. Chem. 2001, 5, 719-755.
31. (c) Zanoni, G.; Castronovo, F.; Franzini, M.; Vidari, G.; Giannini, E. Chem. Soc. Rev. 2003, 32, 115-129.
32. For Pd-catalyzed phosphination using aryl bromides and chlorides, see: Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397-7403.
33. (a) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
34. (b) McDaniel, D. H.; Brown, H. C. J. Org. Chem. 1958, 23, 420-427.
35. Yoshifuji, M.; Shibayama, K.; Inamoto, N. Chem. Lett. 1984, 115-118.
36. Blank, N. F.; McBroom, K. C.; Glueck, D. S.; Kassel, W. S.; Rheingold, A. L. Organometallics 2006, 25, 1742-1748.
37. Kyba, E. P.; Rines, S. P. J. Org. Chem. 1982, 47, 4800-4801.
38. For the analogous Pt complexes, see: (a) ref 5a
39. (b) Scriban, C.; Glueck, D. S.; DiPasquale, A. G.; Rheingold, A. L. Organometallics 2006, 25, 5435-5448.
40. (a) Wisner, J. M.; Bartczak, T. J.; Ibers, J. A.; Low, J. J.; Goddard, W. A., III. J. Am. Chem. Soc. 1986, 108, 347-348.
41. (b) Wisner, J. M.; Bartczak, T. J.; Ibers, J. A. Organometallics 1986, 5, 2044-2050.
42. (c) Oberhauser, W.; Stampfl, T.; Bachmann, C.; Haid, R.; Langes, C.; Kopacka, H.; Ongania, K.-H.; Bruggeller, P. Polyhedron 2000, 19, 913-923.
43. Scriban, C.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Organometallics 2007, 26, 1788-1800.
44. (a) Wicht, D. K.; Glueck, D. S.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1999, 18, 5130-5140.
45. (b) Wicht, D. K.; Kovacik, I.; Glueck, D. S.; Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141-5151.
46. (c) Zhuravel, M. A.; Glueck, D. S.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2002, 21, 3208-3214.
47. 8, -70°C, δ -24.7 (dd, J = 117, 35 Hz)). We could not detect the analogous Me-Duphos resonances or tell if this material was a diastereomer of 5a-c or an impurity; this signal disappeared on warming. For more details on independent generation of the other potential impurities Pd((R,R)-Me-Duphos)(Ph)(PHIs) and Pd((R,R)-Me-Duphos)(Me)(PPhIs), see the Supporting Information.
48. 2 at room temperature.
49. Reaction mixtures with PhOTf contained 1 equiv of NaI per Pd, derived from precursor 3. Independent generation of Pd((R,R)-Me-Duphos)(Ph)-(OTf) (from Pd((R,R)-Me-Duphos)(trans-stilbene) and PhOTf) in the presence of NaI gave 3, consistent with the observations in the catalytic system.
50. Alcazar-Roman, L. M.; Hartwig, J. F. Organometallics 2002, 21, 491-502.
51. 16,19
52. Halpern, J. Science 1982, 217, 401-407.
53. Seeman, J. R. Chem. Rev. 1983, 83, 83-134.
54. For an application in organometallic chemistry, see: Gately, D. A.; Norton, J. R. J. Am. Chem. Soc. 1996, 118, 3479-3489.
55. For a related experiment involving alkylation of Fe-phosphido complexes, see: Crisp, G. T.; Salem, G.; Wild, S. B.; Stephens, F. S. Organometallics 1989, 8, 2360-2367.
56. Small variations in er were observed; see the Supporting Information for results and estimation of the error in measurement of er.
57. Cations 4a and 4b might interconvert by dissociation of PHMe(Is), racemization of the phosphine by reversible deprotonation/protonation, and rebinding (Bader, A.; Nullmeyers, T.; Pabel, M.; Salem, G.; Willis, A. C.; Wild, S. B. Inorg. Chem. 1995, 34, 384-389). If this process occurred very quickly, and one of the diastereomeric cations was deprotonated more rapidly than the other, then it is possible that er ≠ dr in Scheme 6, even if reductive elimination was faster than inversion. However, the lack of dependence of the ee in the catalytic reactions on the concentration or the nature of the base (Table 1, entries 11-14) suggests that the base, and, specifically, the deprotonation step, does not affect enantioselectivity.
58. (a) Moncarz, J. R.; Brunker, T. J.; Glueck, D. S.; Sommer, R. D.; Rheingold, A. L. J. Am. Chem. Soc. 2003, 125, 1180-1181.
59. (b) Reference 6b.
60. WH can be measured by observing decay of either diastereomer of starting material 5, as a complement to the more usual method, observing product formation,
61. -kt) respectively for the first-order formation of B from A. See the Supporting Information for more details.
62. The different precursors yielded 5 along with the byproducts NaOTf and NaI, respectively. While it is possible that the presence of these salts might lead to different rates of reductive elimination, our data are indistinguishable within experimental error.
63. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860.
64. 32 and determining which diastereomer of 5 leads to the major product, however, it is not necessary to determine these numbers with great precision.
65. (a) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754.
66. (b) Drexler, H.-J.; Baumann, W.; Schmidt, T.; Zhang, S.; Sun, A.; Spannenberg, A.; Fischer, C.; Buschmann, H.; Heller, D. Angew. Chem., Int. Ed. 2005, 44, 1184-1188.
67. (c) Schmidt, T.; Baumann, W.; Drexler, H.-J.; Arrieta, A.; Heller, D.; Buschmann, H. Organometallics 2005, 24, 3842-3848.
68. Widenhoefer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6504-6511.
69. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
70. Kondo, Y.; Manabu, S.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539-3540.
71. Barluenga, J.; Gonzalez, J. M.; Garcia-Martin, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058-2060.
72. Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502-2505.
73. Lo Sterzo, C.; Miller, M. M.; Stille, J. K. Organometallics 1989, 8, 2331-2337.
74. Tani, K.; Brown, L. D.; Ahmed, J.; Ibers, J. A.; Nakamura, A.; Otsuka, S.; Yokota, M. J. Am. Chem. Soc. 1977, 99, 7876-7886.
75. Olmstead, M. M.; Power, P. P. J. Organomet. Chem. 1991, 408, 1-6.
76. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030-3039.
77. Kruis, D.; Markies, B. A.; Canty, A. J.; Boersma, J.; van Koten, G. J. Organomet. Chem. 1997, 532, 235-242.