The first examples of ring-closing olefin metathesis of vinyl chlorides

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2505-2507

  Chao, Wenchun ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CHLORIDE; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; RING CLOSING METATHESIS;

ALKENES; VINYL CHLORIDE;

EID: 0141854289     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034775z     Document Type: Article

References (23)

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2. For recent reviews of olefin metathesis see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
3. For recent reviews of olefin metathesis see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
4. For recent reviews of olefin metathesis see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
5. For recent reviews of olefin metathesis see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
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7. See, for example: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623. Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179. Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023. Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029. van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311. Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
8. See, for example: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623. Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179. Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023. Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029. van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311. Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
9. See, for example: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623. Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179. Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023. Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029. van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311. Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
10. See, for example: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623. Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179. Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023. Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029. van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311. Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
11. See, for example: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623. Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179. Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023. Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029. van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311. Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
12. See, for example: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623. Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179. Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023. Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029. van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311. Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
13. See, for example: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623. Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179. Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023. Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029. van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311. Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
14. See, for example: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565. Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310. Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623. Rainier, J. D.; Cox, J. M.; Allwein, S. P. Tetrahedron Lett. 2001, 42, 179. Okada, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 8023. Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029. van Otterlo, W. A. L.; Ngidi, E. L.; Coyanis, E. M.; de Koning, C. B. Tetrahedron Lett. 2003, 44, 311. Whitehead, A.; Moore, J. D.; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
15. Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H. ; Rutjes, F. P. J. T. Org. Lett. 2001, 3, 2045.
16. For a discussion see: Geissert, A. J.; Snyder, L.; Markham, J.; Diver, S. T. Org. Lett. 2003, 5, 1793 and references cited.
17. Louie, J.; Grubbs, R. H. Organometallics 2002, 21, 2153.
18. General experimental procedure for RCM of vinyl chlorides: A 100-mL flask equipped with a condenser was flame dried in vacuo. The vinyl chloride substrate (0.24 mmol) in dry benzene (60 mL) was added and the solution was deaerated by bubbling argon through the mixture for 2 h. Second-generation Grubbs catalyst 2 (10 mol %) in 2 mL of dry benzene was added through the condenser and the argon bubbling was continued for an additional 30 min. The mixture was heated and stirred at 65°C for 4-10 h until TLC showed the reaction was complete. The solvent was removed in vacuo and the residue was purified by silica gel chromatography to afford the desired metathesis product.
19. At room temperature no metathesis occurs, and at 50°C the reaction is very slow.
20. For recent reviews see: Miyaura, N., Ed. Top. Curr. Chem. 2002, 219.
21. (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
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23. VanBrunt, M. P.; Ambenge, R. O.; Weinreb, S. M. J. Org. Chem. 2003, 68, 3323 and references cited therein.