Allylsilanes as carbon nucleophiles in the palladium-catalyzed 1,4-oxidation of conjugated dienes

Chemistry - A European Journal

Volumn 3, Issue 3, 1997, Pages 482-490

  Castaño, Ana M ^a   Persson, B Anders ^a   Bäckvall, Jan E ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

allylsilanes; catalysis; cyclizations; oxidations; palladium

Indexed keywords

EID: 0031004898     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030320     Document Type: Article

References (90)

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28. II-promoted nucleophilic additions to olefins has only been described with stoichiometric amounts of palladium. For a recent review see: Ref. [2c]: see also: G. J. Laidig, L. S. Hegedus, Synthesis 1995, 527.
29. For a related palladium(II)-catalyzed C-C bond formation by insertion of an olefin into a vinylpalladium species generated in situ see: a) S. Ma, X. Lu, J. Chem. Soc. Chem. Commun. 1990, 733; b) S. Ma, X. Lu, J. Org. Chem. 1991. 56, 5120; c) J. Ji, X. Lu, Synlett, 1993, 745.
30. For a related palladium(II)-catalyzed C-C bond formation by insertion of an olefin into a vinylpalladium species generated in situ see: a) S. Ma, X. Lu, J. Chem. Soc. Chem. Commun. 1990, 733; b) S. Ma, X. Lu, J. Org. Chem. 1991. 56, 5120; c) J. Ji, X. Lu, Synlett, 1993, 745.
31. For a related palladium(II)-catalyzed C-C bond formation by insertion of an olefin into a vinylpalladium species generated in situ see: a) S. Ma, X. Lu, J. Chem. Soc. Chem. Commun. 1990, 733; b) S. Ma, X. Lu, J. Org. Chem. 1991. 56, 5120; c) J. Ji, X. Lu, Synlett, 1993, 745.
32. For some recent reviews on allylsilanes, see: a) The Chemistry of Organic Silicon Compounds, Part 2 (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1989; b) I. Fleming, J. Dunogues, R. Smithers, Org. React. 1989, 37, 57-575; c) I. Fleming, Tetrahedron 1988, 44, 3761-4292.
33. For some recent reviews on allylsilanes, see: a) The Chemistry of Organic Silicon Compounds, Part 2 (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1989; b) I. Fleming, J. Dunogues, R. Smithers, Org. React. 1989, 37, 57-575; c) I. Fleming, Tetrahedron 1988, 44, 3761-4292.
34. For some recent reviews on allylsilanes, see: a) The Chemistry of Organic Silicon Compounds, Part 2 (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1989; b) I. Fleming, J. Dunogues, R. Smithers, Org. React. 1989, 37, 57-575; c) I. Fleming, Tetrahedron 1988, 44, 3761-4292.
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37. Allylsilanes have been shown to react with cationic (pentadienyl, trienyl, and allylic) organometallic complexes: a) L. A. P. Kane-Maguire, E. D. Honig, D. A. Swigart, Chem. Rev. 1984, 84, 525-543; b) M. Franck-Neumann, P. Bissinger, P. Geoffroy, Tetrahedron Lett. 1993, 34, 4643-4646; c) B. M. Trost, E. Keinan, ibid. 1980, 21. 2595-2598; d) M. Terakado, M. Miyazawa, K. Yamamoto. Synlett 1994, 134-136.
38. Allylsilanes have been shown to react with cationic (pentadienyl, trienyl, and allylic) organometallic complexes: a) L. A. P. Kane-Maguire, E. D. Honig, D. A. Swigart, Chem. Rev. 1984, 84, 525-543; b) M. Franck-Neumann, P. Bissinger, P. Geoffroy, Tetrahedron Lett. 1993, 34, 4643-4646; c) B. M. Trost, E. Keinan, ibid. 1980, 21. 2595-2598; d) M. Terakado, M. Miyazawa, K. Yamamoto. Synlett 1994, 134-136.
39. Allylsilanes have been shown to react with cationic (pentadienyl, trienyl, and allylic) organometallic complexes: a) L. A. P. Kane-Maguire, E. D. Honig, D. A. Swigart, Chem. Rev. 1984, 84, 525-543; b) M. Franck-Neumann, P. Bissinger, P. Geoffroy, Tetrahedron Lett. 1993, 34, 4643-4646; c) B. M. Trost, E. Keinan, ibid. 1980, 21. 2595-2598; d) M. Terakado, M. Miyazawa, K. Yamamoto. Synlett 1994, 134-136.
40. Allylsilanes have been shown to react with cationic (pentadienyl, trienyl, and allylic) organometallic complexes: a) L. A. P. Kane-Maguire, E. D. Honig, D. A. Swigart, Chem. Rev. 1984, 84, 525-543; b) M. Franck-Neumann, P. Bissinger, P. Geoffroy, Tetrahedron Lett. 1993, 34, 4643-4646; c) B. M. Trost, E. Keinan, ibid. 1980, 21. 2595-2598; d) M. Terakado, M. Miyazawa, K. Yamamoto. Synlett 1994, 134-136.
41. a) J. E. Nyström, T. Rein, J. E. Bäckvall, Org. Synth. 1989, 67, 105-113;
42. b) Prepared from (Z)-4-acetoxy-2-buten-1-ol: K. C. Nicolaou, C. A. Veale, S. E. Webber, H. Katerinopoulos, J. Am. Chem. Soc. 1985, 107, 7515-7518.
43. a) D. J. Ager, I. Fleming, S. K. Patel, J. Chem. Soc. Perkin Trans. 1 1981, 2520-2526; I. Fleming, D. Higgins, N. J. Lawrence, A. P. Thomas, J. Chem. Soc. Perkin Trans. 1 1992, 3331-3349;
44. a) D. J. Ager, I. Fleming, S. K. Patel, J. Chem. Soc. Perkin Trans. 1 1981, 2520-2526; I. Fleming, D. Higgins, N. J. Lawrence, A. P. Thomas, J. Chem. Soc. Perkin Trans. 1 1992, 3331-3349;
45. b) G. Majetich, J. Defauw, Tetrahedron 1988, 44, 3833-3849.
46. For a recent review on the preparation of allylic silanes, see: T. K. Sarkar, Synthesis 1990, 969 and 1101.
47. 2Me.
48. For an excellent study on the effect of gem-dialkyl substitution in cyclization reactions see: M. E. Jung, J. Gervay, J. Am. Chem. Soc. 1991, 113, 224-232.
49. L. E. Overman, F. M. Knoll, Tetrahedron Lett. 1979, 321-324.
50. Descriptors α and β refer to the orientation of the vinyl substituent at C-9 relative to the plane of the molecule.
51. 2Me).
52. 1H NMR spectrum. The complex consists of dimeric diastereoisomers (1:1).
53. II complexes forming the corresponding (π-allyl)-palladium complex, by transfer of the allyl group: J. M. Kliegman, J. Organomet. Chem. 1971, 29, 73-77; T. Hayashi, M. Konishi, M. Kumada, J. Chem. Soc. Chem. Commun. 1983, 736-737; S. Ogoshi, W. Yoshida, K. Ohe, S. Murai, Organometallics 1993, 12, 578-579 and references therein.
54. II complexes forming the corresponding (π-allyl)-palladium complex, by transfer of the allyl group: J. M. Kliegman, J. Organomet. Chem. 1971, 29, 73-77; T. Hayashi, M. Konishi, M. Kumada, J. Chem. Soc. Chem. Commun. 1983, 736-737; S. Ogoshi, W. Yoshida, K. Ohe, S. Murai, Organometallics 1993, 12, 578-579 and references therein.
55. II complexes forming the corresponding (π-allyl)-palladium complex, by transfer of the allyl group: J. M. Kliegman, J. Organomet. Chem. 1971, 29, 73-77; T. Hayashi, M. Konishi, M. Kumada, J. Chem. Soc. Chem. Commun. 1983, 736-737; S. Ogoshi, W. Yoshida, K. Ohe, S. Murai, Organometallics 1993, 12, 578-579 and references therein.
56. 0-catalyzed cross-coupling reactions in which the allyl group is transferred to palladium in an arylpalladium(II) species: Y. Hatanaka, K.-i. Goda, T. Hiyama, Tetrahedron Lett. 1994, 35, 1279-1282; Y. Hatanaka, Y. Ebina, T. Hiyama, J. Am. Chem. Soc. 1991, 113, 7075-7076; L. F. Tietze, R. Schimpf, Angew. Chem. Int. Ed. Engl. 1994, 33, 1089; L. F. Tietze, T. Raschke, Synlett 1995, 599.
57. 0-catalyzed cross-coupling reactions in which the allyl group is transferred to palladium in an arylpalladium(II) species: Y. Hatanaka, K.-i. Goda, T. Hiyama, Tetrahedron Lett. 1994, 35, 1279-1282; Y. Hatanaka, Y. Ebina, T. Hiyama, J. Am. Chem. Soc. 1991, 113, 7075-7076; L. F. Tietze, R. Schimpf, Angew. Chem. Int. Ed. Engl. 1994, 33, 1089; L. F. Tietze, T. Raschke, Synlett 1995, 599.
58. 0-catalyzed cross-coupling reactions in which the allyl group is transferred to palladium in an arylpalladium(II) species: Y. Hatanaka, K.-i. Goda, T. Hiyama, Tetrahedron Lett. 1994, 35, 1279-1282; Y. Hatanaka, Y. Ebina, T. Hiyama, J. Am. Chem. Soc. 1991, 113, 7075-7076; L. F. Tietze, R. Schimpf, Angew. Chem. Int. Ed. Engl. 1994, 33, 1089; L. F. Tietze, T. Raschke, Synlett 1995, 599.
59. 0-catalyzed cross-coupling reactions in which the allyl group is transferred to palladium in an arylpalladium(II) species: Y. Hatanaka, K.-i. Goda, T. Hiyama, Tetrahedron Lett. 1994, 35, 1279-1282; Y. Hatanaka, Y. Ebina, T. Hiyama, J. Am. Chem. Soc. 1991, 113, 7075-7076; L. F. Tietze, R. Schimpf, Angew. Chem. Int. Ed. Engl. 1994, 33, 1089; L. F. Tietze, T. Raschke, Synlett 1995, 599.
60. II led mainly to the recovery of the starting material (≈ 50%), contaminated with unknown by-products and very small amounts of 30.
61. a) G. Zhu, S. Ma, X. Lu, Q. Huang, J. Chem. Soc. Chem. Commun. 1995, 271 -273;
62. - from the least encumbered side (exo, anti to Pd) [31c];
63. c) A. Castaño, unpublished results. (Equation Presented)
64. The relative stereochemistry of the products could not be assigned in the chlorides and was determined in the bipyridine triflate complex.
65. It is known that quinone-induced chloride attack on (π-allyl)palladium complexes occurs anti, see Refs. [7] and [8b].
66. a) A. Albinati, C. J. Ammann, R. W. Kunz, P. S. Pregosin, Organometallics 1991, 10, 1800-1806;
67. b) A. Gogoll, H. Grennberg, Magn. Reson. Chem. 1993, 31, 954;
68. c) A. Gogoll, J. Gomes, M. Bergkvist, H. Grennberg, Organometallics 1995, 14, 1354;
69. d) J. L. Bookham, W. McFarlane, J. Chem. Soc. Chem. Commun. 1993, 1352.
70. The formation of 33α and 33β as the only observable products eliminates an additional alternative pathway for formation of 19, namely, chloropalladation of the diene and subsequent attack by the silane on the (π-allyl)palladium complex (cf. Ref. [18c,d]).
71. 2: B. H. Lipshutz, E. L. Ellsworth, S. T. Dimock, D. C. Reuter, Tetrahedron Lett. 1989, 30, 2065-2068.
72. 2 is not a very suitable source of palladium for this reaction (see Ref. [29a]).
73. The other two compounds have not been characterized. One of the other products has a vinyl group, but it is not clear whether it is a π-allyl complex or if it comes from protonolysis of the allyltin.
74. 3N, and none of the other regioisomer was observed, however, ca. 30% of the conjugated isomer was formed.
75. J. E. Bäckvall, J. O. Vågberg, C. Zercher, J. P. Genêt, A. Denis, J. Org. Chem. 1987, 52, 5430-5435.
76. J. E. Nyström, J. E. Bäckvall, J. Org. Chem. 1983, 48, 3947.
77. Described in: F. Camps, V. Gasol, A. Guerrero, Synthesis 1987, 511.
78. Described in: G. Magnusson, F. Lindqvist, J. Chem. Soc. Chem. Commun. 1990, 1080.
79. Prepared from the commercially available 2-methylene-1,3-propanediol.
80. Y. M. L. Nilsson, P. G. Andersson, J. E. Bäckvall, J. Am, Chem. Soc. 1993, 115, 6609.
81. All signals correspond to both diastereoisomers.
82. Shifts in brackets correspond to the other set of signals, not necessarily to the other isomer, as they have not been assigned.
83. A mixture 16/17 (≈ 1:1) was obtained, contaminated with small amounts of internal Diels-Alder reaction product.
84. Spectral data from mixture of isomers.
85. Some assignments were carried out with the help of 1DTOCSY experiments.
86. Chemical shifts determined from the cross-peak of a relay experiment.
87. Spectral data of30α and 30β from the mixture of isomers. In some cases, the coupling constants were measured from IDTOCSY spectra.
88. Chemical shifts referred to acetone shift at δ = 2.05.
89. Prepared using Ag(OTf) instead of Tl(OTf), see Ref. [34].
90. Chemical shifts referred to methanol shift at δ = 4.87.