Activation of Low-Valent Titanium Reagents with Iodine: Facile Low-Temperature McMurry Reaction and N/O-Debenzylation/Deallylation

Journal of Organic Chemistry

Volumn 63, Issue 15, 1998, Pages 4925-4929

  Talukdar, Sanjay ^a   Nayak, Sandip K ^a   Banerji, Asoke ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001607109     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971751v     Document Type: Article

References (34)

1. (a) Dams, R.; Malinowski, M.; Westdorp, I.; Geise, Y. H. J. Org. Chem. 1982, 47, 248.
2. (b) Nayak, S. K.; Banerji, A. J. Org. Chem. 1991, 56, 1940.
3. (c) Dushin, R. G. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 1071 and references therein.
4. (d) Szymoniak, J.; Besancon, J.; Moïse, C. Tetrahedron 1992, 48, 3867.
5. (a) Banerji, A.; Nayak, S. K. J. Chem. Soc., Chem. Commun. 1990, 150.
6. (b) Nayak, S. K; Kadam, S. M.; Talukdar, S.; Banerji, A. J. Indian Inst. Sci. 1994, 74, 401.
7. (c) Talukdar, S.; Nayak, S. K.; Banerji, A. Full. Sci. Technol. 1995, 3, 327.
8. (d) Balu, N.; Nayak, S. K.; Banerji, A. J. Am. Chem. Soc. 1996, 118, 5932 and references therein.
9. (e) Talukdar, S. Ph.D. Thesis, 1997, University of Mumbai, Mumbai, India.
10. Lipski, T. A.; Hilfiker, M. A.; Nelson, S. G. J. Org. Chem. 1997, 62, 4566.
11. (a) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877 and references therein.
12. (b) Hirao, T. Chem. Rev. 1997, 97, 2707 and references therein.
13. (a) McMurry, J. E. Chem. Rev. 1989, 89, 1513.
14. (b) Fürstner, A.; Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2442 and references therein.
15. (a) McMurry, J. E.; Rico, J. G. Tetrahedron Lett. 1989, 30, 1169.
16. (b) McMurry, J. E.; Dushin, R. G. J. Am. Chem. Soc. 1990, 112, 6942.
17. (a) Fürstner, A.; Weidmann, H. Synthesis 1987, 1071.
18. (b) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729.
19. (c) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
20. (a) Cintas, P. Activated Metals in Organic Synthesis; CRC Press: Boca Raton, 1993.
21. (b) Fürstner, A. Active Metals-Preparation, Characterization, Applications; VCH: Weinheim, 1996 and references therein.
22. McMurry, J. E.; Fleming, M. P.; Kees, K. L.; Krepski, L. R. J. Org. Chem. 1978, 43, 3255.
23. (a) Tyrlik, S.; Wolochowicz, I. J. Chem. Soc., Chem. Commun. 1975, 781.
24. (b) Talukdar, S.; Banerji, A. Synth. Commun. 1995, 25, 813.
25. (c) Talukdar, S.; Banerji, A. Synth. Commun. 1996, 26, 1051.
26. Isomeric ratio of 3a are established using spectroscopic data, see: Andersson, P. G. Tetrahedron Lett. 1994, 35, 2609.
27. (a) Kadam, S. M.; Nayak, S. K.; Banerji, A. Tetrahedron Lett. 1992, 33, 5129.
28. (b) Nayak, S. K.; Kadam, S. M.; Banerji, A. Synlett. 1993, 581.
29. Akiyama, T.; Hirofuji, H.; Ozaki, S. Tetrahedron Lett. 1991, 32, 1321.
30. Ketcha, D. M.; Lieurance, B. A.; Homan, D. F. J. J. Org. Chem. 1989, 54, 4350.
31. (a) Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd ed.; John Wiley & Sons: New York, 1991.
32. (b) Sujuki, H.; Tsukuda, A.; Konda, M.; Aizawa, M.; Senoo, Y.; Nakajima, M.; Watanabe, T.; Yokoyama, Y.; Murakami, Y. Tetrahedron Lett. 1995, 36, 1671.
33. --systems are -1.63 V and +0.54 V respectively, see: Braun, R. D. Introduction to Instrumental Analysis; McGraw-Hill International Edition: New York, 1987; p 700.
34. Lai, Y.-H. Synthesis 1981, 585.