Preparation of allyl-, alkenyl- and of functionalized arylmanganese reagents by oxidative insertion of manganese-graphite into organic halides

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7009-7012

  Fürstner, Alois ^a   Brunner, Heiko ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MANGANESE; ORGANOMETALLIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030599259     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01591-2     Document Type: Article

References (26)

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2. (b) Cahiez, G. in Encyclopedia of Reagents for Organic Synthesis (Paquette, L. A., Ed.), Wiley, New York 1995, 925-928 and 3227-3229
3. (c) Normant, J.-F.; Cahiez, G. in Modern Synthetic Methods (Scheffold, R.; Ed.), Sauerländer-Salle, Frankfurt, 1983, Vol. 3, 173-216.
4. (d) Kasatkin, A. N.; Tsypyshev, O. Y.; Romanova, T. Y.; Tolstikov, G. A., Russ. Chem. Rev. 1992, 61, 537-549 and lit. cit.
5. 2. For some recent advancements see: (a) Cahiez, G.; Marquais, S. Tetrahedron Lett. 1996, 1773-1776.
6. (b) Klement, I.; Knochel, P.; Chau, K.; Cahiez, G. Tetrahedron Lett. 1994, 1177-1180.
7. (c) Reetz, M. T., Haning, H.; Stanchev, S. Tetrahedron Lett. 1992, 6963-6966.
8. 3SiMnX see: Fürstner, A.; Weidmann, H. J. Organomet. Chem. 1988, 354, 15-21.
9. - ↔ Mn (-1.03V), c.f. Handbook of Chemistry and Physics, 62nd Ed., CRC Press, Boca Raton, FL, 1982.
10. 4. For the application of commercial Mn as mediator of Cr(2+)-catalyzed Nozaki-Hiyama reactions see: Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533-2534.
11. 5. Hiyama, T.; Sawahata, M.; Obayashi, M. Chem. Lett. 1983, 1237-1238.
12. 6. Cahiez, G.; Chavant, P.-Y. Tetrahedron Lett. 1989, 7373-7376.
13. 7. Pugin, B.; Turner, A. T. Adv. Sonochem. 1990, 1, 81-118.
14. 8. Hiyama, T.; Obayashi, M.; Nakamura, A. Organometallics 1982, 1, 1249-1251.
15. 9. Kim, S.-H.; Hanson, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 2197-2200.
16. 2·nLiBr in transmetallations see: Cahiez, G.; Laboue, B. Tetrahedron Lett. 1989, 3545-3546.
17. 4 see: Aubry, J.; Monnier, G. Compt. Rend. Acad. Sci. 1954, 238, 2534-2535. No synthetic applications, however, were reported.
18. 11. Reviews: (a) Fürstner, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 164-189.
19. (b) Active Metals. Preparation, Characterization, Applications (Fürstner, A.; Ed.), VCH, Weinheim, 1996, 381-426.
20. 12. For related zincations of aryl halides with Zn(Ag)-graphite see: Fürstner, A., Singer, R.; Knochel, P. Tetrahedron Lett. 1994, 1047-1050.
21. 8K; (ii) the morphological conclusions reached in this paper have been clearly disproved for a variety of other metal-graphite combinations, c.f. Fürstner, A.; Weidmann, H.; Hofer, F. J. Chem. Soc. Dalton Trans. 1988, 2023-2026; Review: Hofer, F. in Active Metals. Preparation, Characterization, Applications (Fürstner, A.; Ed.), VCH, Weinheim, 1996, 427-446.
22. 8K; (ii) the morphological conclusions reached in this paper have been clearly disproved for a variety of other metal-graphite combinations, c.f. Fürstner, A.; Weidmann, H.; Hofer, F. J. Chem. Soc. Dalton Trans. 1988, 2023-2026; Review: Hofer, F. in Active Metals. Preparation, Characterization, Applications (Fürstner, A.; Ed.), VCH, Weinheim, 1996, 427-446.
23. 8K; (ii) the morphological conclusions reached in this paper have been clearly disproved for a variety of other metal-graphite combinations, c.f. Fürstner, A.; Weidmann, H.; Hofer, F. J. Chem. Soc. Dalton Trans. 1988, 2023-2026; Review: Hofer, F. in Active Metals. Preparation, Characterization, Applications (Fürstner, A.; Ed.), VCH, Weinheim, 1996, 427-446.
24. 14. For a pertinent discussion see: Hoffmann, R. W. Angew. Chem. 1982, 94, 569-580.
25. 15. Arai, I.; Daves, G. D. J. Chem. Soc. Chem. Commun. 1976, 69-70.
26. 3): δ -140.1 (vt, J = 7), -152.0 (t, J = 19), -160.8 (dt, J = 7, 19).