Platinum-catalyzed nucleophilic addition of vinylsilanes at the β-position

Organic Letters

Volumn 11, Issue 21, 2009, Pages 5066-5069

  Miura, Katsukiyo ^a   Inoue, Gen ^b   Sasagawa, Hisashi ^b   Kinoshita, Hidenori ^a   Ichikawa, Junji ^b   Hosomi, Akira ^b  

^a SAITAMA UNIVERSITY   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70350635768     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902060r     Document Type: Article

References (26)

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3. (a) Denmark, S. E.; Sweis, R. F. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; De Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; p 163.
4. (b) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; p 421.
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6. (b) Blumenkopf, T. A.; Look, G. C.; Overman, L. E. J. Am. Chem. Soc. 1990, 112, 4399.
7. (a) Ikenaga, K.; Kikukawa, K.; Matsuda, T. J. Chem. Soc, Perkin Trans. 1 1986, 1959.
8. (b) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845.
9. For the Pt(II)-catalyzed reaction of aldehydes with allylsilanes, see: Fürstner, A.; Voigtländer, D. Synthesis 2000, 959.
10. Miura, K.; Itaya, R.; Horiike, M.; Izumi, H.; Hosomi, A. Synlett 2005, 3148.
11. 2O) showed no catalytic activity.
12. 2.
13. (a) Hartley, F. R. In Comprehensive Organometallic Chemistry I; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Elsevier: Oxford, 1982; Vol.6, p 471.
14. (b) Anderson G. K. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds; Elsevier: Oxford, 1995; Vol.9, p 431.
15. 2]). Haschke, E. M.; Fitch, J. W. J. Organomet. Chem. 1973, 57, C93.
16. 2-C-Si bond in vinylsilanes by Pt(II) complexes, see ref 9 and the following references: (a) Mansuy, D.; Pusset, J.; Chottard, J. C. J. Organomet. Chem. 1976, 110, 139.
17. (b) Poist, J. E.; Kraihanzel, C. S. Chem. Commun. 1968, 607.
18. Some vinyl-transition metals are known to react with carbon electrophiles at the β-position to give carbene complexes. Kusama, H.; Yamabe, H.; Onizawa, Y.; Hoshino, T.; Iwasawa, N. Angew. Chem., Int. Ed. 2005, 44, 468, and references cited therein.
19. The transformation of Pt-carbene complexes into alkenes has been proposed as a key step of the Pt(II)-catalyzed cycloisomerization of 1,6enynes. (a) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc: 2000, 122, 6785.
20. (b) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704.
21. (c) Echavarren, A. M.; Méndez, M.; Muñoz, M. P.; Nevado, C.; Martín-Matute, B.; Nieto-Oberhuber, C.; Cárdenas, D. J. Pure Appl. Chem. 2004, 76, 453.
22. For protonation of vinylplatinum complexes to carbene complexes, see: Bell, R. A.; Chisholm, M. H.; Couch, D. A.; Rankel, L. A. Inorg. Chem. 1977, 16, 677.
23. The Pt(II)-catalyzed reaction of diazo compounds with alcohols is known to give ethers by insertion into the O-H bond, which proceeds probably via Pt-carbene complexes, (a) Bertani, R.; Biasiolo, M.; Darini, K.; Michelin, R. A.; Mozzon, M.; Visentin, F.; Zanotto, L. J. Organomet. Chem. 2002, 642, 32.
24. (b) Schils, R.; Simal, F.; Demonceau, A.; Noels, A. F.; Eremenko, I. L.; Sidorov, A. A.; Nefedov, S. E. Tetrahedron Lett. 1998, 39, 7849.
25. Approximately one of two methylene hydrogens was displaced by deuterium in both the α-β and -positions.
26. The Hiyama cross-coupling reactions of vinylsilanes generally requires a heteroatom-substituted silyl group (or its precursor) and a stoichiometric activator such as a fluoride ion. See ref 2. Narasaka and co-workers have recently reported an example of the catalytic C-C bondforming reaction of the TMS-protected vinyl donor without any stoichiometric activators. Yamane, M.; Uera, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 2005, 78, 477.