Application of fluoride-catalyzed silane reductions of tin halides to the in situ preparation of vinylstannanes

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5958-5965

  Maleczka Jr , Robert E ^a   Terrell, Lamont R ^a   Clark, Damon H ^a   Whitehead, Susan L ^a   Gallagher, William P ^a   Terstiege, Ina ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; OXIDATION REDUCTION REACTION; STRUCTURE ANALYSIS;

EID: 0345426367     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990491+     Document Type: Article

References (52)

1. Terstiege, I.; Maleczka, R. E., Jr. J. Org. Chem. 1999, 64, 342-343.
2. Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448.
3. For other methods of generating trialkyltin hydrides, see: (a) Chemistry of Tin; Smith, P. J., Ed.; Blackie Academic & Professional: New York, 1998. (b) Pereyre, M.; Quintard, J.-P.; Rahm, A. In Tin in Organic Synthesis; Butterworth: Toronto, 1987. Via PMHS reduction of tin oxides: (c) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. (d) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1976, 40, 2265-2266. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796-2797. Via silane reduction of tin amides: (f) Hays, D. S.; Fu, G. C. J. Org. Chem. 1997, 62, 7070-7071.
4. For other methods of generating trialkyltin hydrides, see: (a) Chemistry of Tin; Smith, P. J., Ed.; Blackie Academic & Professional: New York, 1998. (b) Pereyre, M.; Quintard, J.-P.; Rahm, A. In Tin in Organic Synthesis; Butterworth: Toronto, 1987. Via PMHS reduction of tin oxides: (c) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. (d) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1976, 40, 2265-2266. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796-2797. Via silane reduction of tin amides: (f) Hays, D. S.; Fu, G. C. J. Org. Chem. 1997, 62, 7070-7071.
5. For other methods of generating trialkyltin hydrides, see: (a) Chemistry of Tin; Smith, P. J., Ed.; Blackie Academic & Professional: New York, 1998. (b) Pereyre, M.; Quintard, J.-P.; Rahm, A. In Tin in Organic Synthesis; Butterworth: Toronto, 1987. Via PMHS reduction of tin oxides: (c) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. (d) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1976, 40, 2265-2266. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796-2797. Via silane reduction of tin amides: (f) Hays, D. S.; Fu, G. C. J. Org. Chem. 1997, 62, 7070-7071.
6. For other methods of generating trialkyltin hydrides, see: (a) Chemistry of Tin; Smith, P. J., Ed.; Blackie Academic & Professional: New York, 1998. (b) Pereyre, M.; Quintard, J.-P.; Rahm, A. In Tin in Organic Synthesis; Butterworth: Toronto, 1987. Via PMHS reduction of tin oxides: (c) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. (d) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1976, 40, 2265-2266. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796-2797. Via silane reduction of tin amides: (f) Hays, D. S.; Fu, G. C. J. Org. Chem. 1997, 62, 7070-7071.
7. For other methods of generating trialkyltin hydrides, see: (a) Chemistry of Tin; Smith, P. J., Ed.; Blackie Academic & Professional: New York, 1998. (b) Pereyre, M.; Quintard, J.-P.; Rahm, A. In Tin in Organic Synthesis; Butterworth: Toronto, 1987. Via PMHS reduction of tin oxides: (c) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. (d) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1976, 40, 2265-2266. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796-2797. Via silane reduction of tin amides: (f) Hays, D. S.; Fu, G. C. J. Org. Chem. 1997, 62, 7070-7071.
8. For other methods of generating trialkyltin hydrides, see: (a) Chemistry of Tin; Smith, P. J., Ed.; Blackie Academic & Professional: New York, 1998. (b) Pereyre, M.; Quintard, J.-P.; Rahm, A. In Tin in Organic Synthesis; Butterworth: Toronto, 1987. Via PMHS reduction of tin oxides: (c) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. (d) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1976, 40, 2265-2266. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796-2797. Via silane reduction of tin amides: (f) Hays, D. S.; Fu, G. C. J. Org. Chem. 1997, 62, 7070-7071.
9. For a general discussion of PMHS-based reductions see Mimoun, H. J. Org. Chem. 1999, 64, 2582-2589 and references therein.
10. Maleczka, R. E., Jr.; Terstiege, I. J. Org. Chem. 1998, 63, 9622-9623.
11. (a) Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881-884.
12. (b) Zhang, H. X.; Guibé, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619-622.
13. (c) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
14. All starting 1-alkynes were purchased from Aldrich except (a) 5-(tert-butyldimethylsilyloxy)-1-pentyne (11) (Marshall, J. A.; DeHoff, B. S. J. Org. Chem. 1986, 51, 863-872), (b) 6-(tert-butyldimethylsilyloxy)-1-hexyne (13) (Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883-2894), (c) 6-aceto-1-hexyne (19) (Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073), and (d) 5-(tetrahydropyranyloxy)-1-pentyne (27) (Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1995, 60, 4595-4601), which were prepared by the methods cited above.
15. All starting 1-alkynes were purchased from Aldrich except (a) 5-(tert-butyldimethylsilyloxy)-1-pentyne (11) (Marshall, J. A.; DeHoff, B. S. J. Org. Chem. 1986, 51, 863-872), (b) 6-(tert-butyldimethylsilyloxy)-1-hexyne (13) (Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883-2894), (c) 6-aceto-1-hexyne (19) (Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073), and (d) 5-(tetrahydropyranyloxy)-1-pentyne (27) (Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1995, 60, 4595-4601), which were prepared by the methods cited above.
16. All starting 1-alkynes were purchased from Aldrich except (a) 5-(tert-butyldimethylsilyloxy)-1-pentyne (11) (Marshall, J. A.; DeHoff, B. S. J. Org. Chem. 1986, 51, 863-872), (b) 6-(tert-butyldimethylsilyloxy)-1-hexyne (13) (Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883-2894), (c) 6-aceto-1-hexyne (19) (Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073), and (d) 5-(tetrahydropyranyloxy)-1-pentyne (27) (Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1995, 60, 4595-4601), which were prepared by the methods cited above.
17. All starting 1-alkynes were purchased from Aldrich except (a) 5-(tert-butyldimethylsilyloxy)-1-pentyne (11) (Marshall, J. A.; DeHoff, B. S. J. Org. Chem. 1986, 51, 863-872), (b) 6-(tert-butyldimethylsilyloxy)-1-hexyne (13) (Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883-2894), (c) 6-aceto-1-hexyne (19) (Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073), and (d) 5-(tetrahydropyranyloxy)-1-pentyne (27) (Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1995, 60, 4595-4601), which were prepared by the methods cited above.
18. Though not consistently reproducible, reactions run in THF produce stannyldienes with proposed structure i in yields as high as 26%. For further details, including the structure elucidation of i, please see the Supporting Information. (equation presented)
19. Although successful, reactions carried out in the absence of TBAF or TBAI ran considerably glower.
20. 1H NMR) from the crude mixture, presumably as a result in part of protiodestannylation during silica gel chromatographic purification (see: Hitchcock, S. A,; Mayhugh, D. R.; Gregory, G. S. Tetrahedron Lett. 1995, 36, 9086-9088 and ref 6c).
21. CsF may be substituted for KF with little change in the outcome of the reaction.
22. Some substrate intolerance was observed when 6-(tert-butyldimethylsilyloxy)-1-hexyne (13) was subjected to conditions A. In this case, although the TBS group remained in place, a significant amount of destannylation occurred.
23. Mitchell, T. N.; Amamria, A.; Killing, H.; Rutechow, D. J. Organomet. Chem. 1986, 304, 257-265.
24. (a) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741-760.
25. (b) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181-1192.
26. (c) Li, C.-J. Chem. Rev. 1993, 93, 2023-2035.
27. (d) Grieco, P. A. Aldrichimica Acta 1991, 24, 59-66.
28. (e) Breslow, R. Acc. Chem. Res. 1991, 6, 159-164.
29. Kawakami, T.; Shibata, I.; Baba, A. J. Org. Chem. 1996, 61, 82-87.
30. 119Sn NMR data is consistent with this hypothesis, as is literature precedent, see: Leibner, J. E.; Jacobus, J. J. Org. Chem. 1979, 44, 449-450.
31. 3SnF and PMHS results in the formation of only trace amounts of stannane.
32. (a) Corey, E. J.; Guzman-Perez, A.; Lazerwith, S. E. J. Am. Chem. Soc. 1997, 119, 11769-11776.
33. (b) Pearlman, B. A.; Putt, S. R.; Fleming, J. A. J. Org. Chem. 1986, 50, 3622-3624.
34. (c) Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737-7745.
35. (d) Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079-4094.
36. 3SnF/TBAF/PMHS protocol.
37. 3SnF/TBAF/PMHS protocol.
38. (a) Reed-Mundell, J. J.; Nadkarni, D. V.; Kunz, J. M., Jr.; Fry, C. W.; Fry, J. L. Chem. Mater. 1995, 7, 1655-1660.
39. (b) Kini, A. D.; Nadkarni, D. V.; Fry, J. L. Tetrahedron Lett. 1994, 35, 1507-1510.
40. (c) For other immobilized hydrosilanes, see: Rudzinski, W. E.; Montgomery, T. L.; Frye, J. S.; Hawkins, B. L.; Maciel, G. E. J. Catal. 1986, 98, 444-456.
41. (a) Scott, W. J.; Moretto, A. F. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. Ed.; Wiley: New York, 1995; Vol. 7, 5327-5328.
42. (b) Dyer, R. S.; Walsh, T. J.; Wonderlin, W. F.; Bercegeay, M. Neurobehav. Toxicol. Teratol. 1982, 4, 127-133.
43. 3a Thus, tin poisoning through absorption is also minimized by this protocol.
44. Boden, C. D. J.; Pattenden, G.; Ye, T. J. Chem. Soc., Perkin Trans. 1 1996, 2417-2419.
45. In our hands, the control experiments gave somewhat lower levels of regio- and stereocontrol than have been reported in the literature (refs 6c and 23). We are not alone in this experience (see: Blaskovich, M. A.; Kahn, M. J. Org. Chem. 1996, 63, 1119-1125).
46. For reasons that remain unclear, working up the palladium-catalyzed hydrostannylations of 2-phenyl-3-butyn-2-ol (7) with NaOH resulted in the intrusive formation (12%) of the homocoupled diene (Alcaraz, L.; Taylor, R. J. K. Synlett 1997, 791-792 and references therein).
47. Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768-7780.
48. Cliff, M. D.; Pyne, S. G. Tetrahedron 1996, 52, 13703-13712.
49. For a prior preparation, boiling point, and IR data for 25, see: Yee, K. C. US Patent 4,125,534, 1978; Chem. Abst. 1979, 90, 88046.
50. For a prior preparation, boiling point, and IR data for 25, see: Yee, K. C. US Patent 4,125,534, 1978; Chem. Abst. 1979, 90, 88046.
51. For a prior preparation of 26, see: Straus, F.; Kollek, L.; Heyn, W. Chem. Ber. 1930, 63, 1868-1885.
52. For a prior preparation of 28 without spectroscopic data, see ref 23.