The first intramolecular pauson-khand reaction in water using aqueous colloidal cobalt nanoparticles as catalysts

Organic Letters

Volumn 4, Issue 2, 2002, Pages 277-279

  Son, Seung Uk ^a   Lee, Sang Ick ^a   Chung, Young Keun ^a   Kim, Sang Wook ^a   Hyeon, Taeghwan ^a  

^a Seoul National University   (South Korea)

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ARTICLE;

EID: 0000266263     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017043k     Document Type: Article

References (22)

1. For recent reviews, see: (a) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (b) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2000, 1657. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297. (d) Jeong, N. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C, Eds.; Wiley-VCH: Weinheim, 1998; p 560. (e) Geis, O.; Schmalz, H.-G. Angew: Chem., Int. Ed. Engl. 1998, 37, 911.
2. For recent reviews, see: (a) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (b) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2000, 1657. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297. (d) Jeong, N. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C, Eds.; Wiley-VCH: Weinheim, 1998; p 560. (e) Geis, O.; Schmalz, H.-G. Angew: Chem., Int. Ed. Engl. 1998, 37, 911.
3. For recent reviews, see: (a) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (b) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2000, 1657. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297. (d) Jeong, N. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C, Eds.; Wiley-VCH: Weinheim, 1998; p 560. (e) Geis, O.; Schmalz, H.-G. Angew: Chem., Int. Ed. Engl. 1998, 37, 911.
4. For recent reviews, see: (a) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (b) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2000, 1657. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297. (d) Jeong, N. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C, Eds.; Wiley-VCH: Weinheim, 1998; p 560. (e) Geis, O.; Schmalz, H.-G. Angew: Chem., Int. Ed. Engl. 1998, 37, 911.
5. For recent reviews, see: (a) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (b) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2000, 1657. (c) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297. (d) Jeong, N. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C, Eds.; Wiley-VCH: Weinheim, 1998; p 560. (e) Geis, O.; Schmalz, H.-G. Angew: Chem., Int. Ed. Engl. 1998, 37, 911.
6. (a) Kim, S.-W.; Son, S. U.; Lee, S.-I.; Hyeon, T.; Chung, Y. K. J. Am. Chem. Soc. 2000, 122, 1550.
7. (b) Son, S. U.; Lee, S.-I.; Chung, Y. K. Angew: Chem., Int. Ed. 2000, 39, 4158.
8. (a) Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
9. (b) Jeona, N.; Hwang, S. H. Angew. Chem., Int. Ed. 2000, 39, 636.
10. (a) Aqueous-Phase Organometallic Catalysis; Comils, B., Herrman, W. A., Eds.; Wiley-VCH: Weinheim, 1998.
11. (b) Katti, K. V.; Gali, H.; Smith, C. J.; Berning, D. E. Acc. Chem. Res. 1999, 32, 9.
12. (c) Herrman, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
13. (d) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Eur. J. Chem. 2001, 439.
14. (e) Genet, J. P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305.
15. (f) Hanson, B. E. Coord. Chem. Rev. 1999, 185-186, 795.
16. Sigman, M. S.; Fatland, A. W.; Eaton, B. E. J. Am. Chem. Soc. 1998, 120, 5130.
17. (a) Ershov, B. G.; Sukhov, N. L.; Janata, E. J. Phys. Chem. B 2000, 104, 6138.
18. (b) Russier, V.; Petit, C.; Legrand, J.; Pileni, M. P. Phys. Rev. B 2000, 62, 3910.
19. 4 (0.4 g, 10 mmol) in 10 mL of water was added dropwise to the mixture. The color of the solution changed immediately from pink to black, indicating the formation of colloidal particles. The resulting solution was used directly in the PK reaction.
20. 4, concentrated, and chromatographed on a silica gel column, eluting with hexane and diethyl ether (v/v, 2:1). Removal of the solvent gave the product in 92% yield (0.11 g). When the catalyst was recycled, excess diethyl ether was added to the reaction mixture after the reaction. The resulting solution was stirred, and the upper layer was pipetted. Removal of the solvent gave the product. The remained aqueous solution was reused for the further catalytic reaction.
21. Manabe, K.; Mori, Y.; Wakabayashi, T.; Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 7202.
22. +) calcd 278.1518, obsd 278.1517