Potassium Hydride as Nucleophile: A Practical Method for Cleavage and Functional Modification of Cr(CO)3-Ar-SiMe3 Bonds

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1901-1905

  Mandal, Sunil K ^a   Sarkar, Amitabha ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001551126     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971856y     Document Type: Article

References (35)

1. Reviews on arene tricarbonylchromium complexes: (a) Semmelhack. M. F. Transition Metal Arene Complexes: Nucleophilic Addition. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A. Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 979. (b) Semmelhack, M. F. Transition Metal Arene Complexes: Ring Lithiation. Ibid, p 1017. (c) Davies, S. G.; McCarthy, T. D. Transition Metal Arene Complexes: Side Chain Activation and Control of Stereochemistry. Ibid. p 1039.
2. Reviews on arene tricarbonylchromium complexes: (a) Semmelhack. M. F. Transition Metal Arene Complexes: Nucleophilic Addition. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A. Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 979. (b) Semmelhack, M. F. Transition Metal Arene Complexes: Ring Lithiation. Ibid, p 1017. (c) Davies, S. G.; McCarthy, T. D. Transition Metal Arene Complexes: Side Chain Activation and Control of Stereochemistry. Ibid. p 1039.
3. Reviews on arene tricarbonylchromium complexes: (a) Semmelhack. M. F. Transition Metal Arene Complexes: Nucleophilic Addition. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A. Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 979. (b) Semmelhack, M. F. Transition Metal Arene Complexes: Ring Lithiation. Ibid, p 1017. (c) Davies, S. G.; McCarthy, T. D. Transition Metal Arene Complexes: Side Chain Activation and Control of Stereochemistry. Ibid. p 1039.
4. Uemura, M. Tricarbonyl (η6-arene) chromium Complexes in Organic Synthesis. In Advances In Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 231-240 and refs 84-110 cited therein.
5. Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans, 1 1990, 393.
6. (a) Mukai, C.; Hirai, S.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1996, 37, 5389.
7. (b) Bisaha, J. J.; Ph.D. Dissertation, Princeton University, 1980.
8. (c) Semmelhack, M. F.; Bisaha, J. J.; Czarny, M. J. Am. Chem. Soc. 1979, 101, 768.
9. (d) Semmelhack, M. F.; Zask, A. J. Am. Chem. Soc. 1983, 105, 2034.
10. (e) Clough, J. M.; Mann, I. S.; Widdowson, D. A. Synlett 1990, 469.
11. Sur, S.; Mandal, S. K.; Sarkar, A. Unpublished result.
12. For fluoride-induced desilylation from uncomplexed aromatic ring: (a) Hayes, M. A. One or More =CH Bond(s) Formed by Substitution or Addition. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, pp 447-448 and refs cited therein. (b) Snieckus, V. Chem. Rev. 1990, 90, 922.
13. For fluoride-induced desilylation from uncomplexed aromatic ring: (a) Hayes, M. A. One or More =CH Bond(s) Formed by Substitution or Addition. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 1, pp 447-448 and refs cited therein. (b) Snieckus, V. Chem. Rev. 1990, 90, 922.
14. For desilylation of electron defficient aromatic ring using potassium tert-butoxide: (a) Effenberger, F.; Spiegier, W. Chem. Ber. 1985, 118, 3900. (b) Effenberger, F.; Schollkopf, K. Angew. Chem., Int. Ed. Engl. 1981, 20, 226. (c) Streitweiser, A.; Boerth, D. W. J. Am. Chem. Soc. 1978, 100, 755.
15. For desilylation of electron defficient aromatic ring using potassium tert-butoxide: (a) Effenberger, F.; Spiegier, W. Chem. Ber. 1985, 118, 3900. (b) Effenberger, F.; Schollkopf, K. Angew. Chem., Int. Ed. Engl. 1981, 20, 226. (c) Streitweiser, A.; Boerth, D. W. J. Am. Chem. Soc. 1978, 100, 755.
16. For desilylation of electron defficient aromatic ring using potassium tert-butoxide: (a) Effenberger, F.; Spiegier, W. Chem. Ber. 1985, 118, 3900. (b) Effenberger, F.; Schollkopf, K. Angew. Chem., Int. Ed. Engl. 1981, 20, 226. (c) Streitweiser, A.; Boerth, D. W. J. Am. Chem. Soc. 1978, 100, 755.
17. Potassium hydride as nucleophile: Pinnick, H. W. Org. Prepn. Proc. Int. 1983, 15(3), 199.
18. (a) Mahaffy, C. A. L.; Pauson, P. L. Inorg. Synth. 1979, 19, 154.
19. (b) Top, S.; Jaouen, G. J. Organomet. Chem. 1979, 182, 381.
20. 81 Carbon Ligands. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 3, p 1001 and refs 214, 216 cited therein.
21. Synthetic uses of some substituted aromatic aldehyde complexes: (a) Sur, S.; Mandai, S. K.; Sarkar, A. Unpublished results, (b) Reference lc pp 1044-1048 and refs cited therein, (c) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088. (d) Mukai, C.; Hirai, S.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1996, 37, 5389.
22. Synthetic uses of some substituted aromatic aldehyde complexes: (a) Sur, S.; Mandai, S. K.; Sarkar, A. Unpublished results, (b) Reference lc pp 1044-1048 and refs cited therein, (c) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088. (d) Mukai, C.; Hirai, S.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1996, 37, 5389.
23. Synthetic uses of some substituted aromatic aldehyde complexes: (a) Sur, S.; Mandai, S. K.; Sarkar, A. Unpublished results, (b) Reference lc pp 1044-1048 and refs cited therein, (c) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088. (d) Mukai, C.; Hirai, S.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1996, 37, 5389.
24. Synthetic uses of some substituted aromatic aldehyde complexes: (a) Sur, S.; Mandai, S. K.; Sarkar, A. Unpublished results, (b) Reference lc pp 1044-1048 and refs cited therein, (c) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088. (d) Mukai, C.; Hirai, S.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1996, 37, 5389.
25. When DMF was used as the solvent, reaction was complete within 2 h. In ether it took more than 5 h for completion.
26. Reference 10, p 1010.
27. 3 anchored on the electron rich phenoxy ring and the second major product is the same as 2g, and in the minor product both rings complexed to Cr(CO).
28. (a) Seyferth, D.; Alleston, D. L. Inorg. Chem. 1963, 2, 417.
29. (b) Effenberger, F.; Schollkopf, K. Chem. Ber. 1985, 118, 4356.
30. (c) Mcfarlane, W.; Grim, S. O. J. Organomet. Chem. 1966, 5, 147.
31. (d) Nicholls, B.; Whiting, M. C. J. Chem. Soc. 1959, 551.
32. (e) Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1989, 192.
33. (f) Mahaffy, C A. L.; Hamilton, J. Synth. React. Inorg. Met. Org. Chem. 1987, 17, 43.
34. (g) Mahaffy, C. A. L. Ibid. 1984, 14, 679.
35. Chowdhury, S. K.; Samanta, U.; Puranik, V. G.; Sarkar, A. Organometallics 1997, 16, 2618.