Reactions of vinyl and aryl triflates with hypervalent tin reagents

Organometallics

Volumn 20, Issue 5, 2001, Pages 1020-1023

  Martínez, Antonio García ^a   Barcina, José Osío ^a   Heras, Maria Del Rosario Colorado ^a   Cerezo, Alvaro De Fresno ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL TRIFLATES; HYPERVALENT TIN REAGENTS; STILLE REACTIONS; TRANSMETALATION; VINYL TRIFLATES;

AGENTS; CATALYSIS; CHEMICAL BONDS; CHEMICAL REACTIONS; TIN COMPOUNDS;

ORGANOMETALLICS;

EID: 0035809965     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000957a     Document Type: Article

References (50)

1. (a) Farina, V.; Krishasmurthy, V.; Scott, W. J. Organic Reactions; Wiley: New York, 1997, Vol. 50
2. (b) Ritter, K. Synthesis 1993, 735.
3. (c) Mitchell, T. N. Synthesis 1992, 903.
4. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25. 508.
5. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 106, 3033.
6. 2/HMPA has been reorted recently: (a) Usse, S.; Guillaumet, G.; Viaud, M.-C. Tetrahedron Lett. 1997, 38, 5501.
7. For reactions of benzyl stannanes with acid chlorides, see: (b) Andrianome, M.; Delmond, B. J. Org. Chem. 1988, 53, 542.
8. (c) Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem. 1988, 48, 4634.
9. (c) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1983, 58, 5434.
10. de Lang, R.-J.; van Hoojdonk, M. J. C. M.; Brandsma, L.; Kramer, H.: Seinen, W. Tetrahedron 1998, 54, 2953.
11. (a) Posner, G. H. Org. React. 1975, 22, 253.
12. (a) Lipshutz, B. H. Synlett 1990, 119.
13. (a) Knochel, P.; Singer, R. D. Chem. Rev. 1983, 92, 2117.
14. (b) Rottländer, M.; Knochel, P. Tetrahedron Lett. 1997, 38, 1749.
15. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
16. (b) Suzuki A. J. Organomet. Chem. 1999, 576, 147.
17. A procedure for the preparation of benzylic and allylic boronates has been recently reported.: Falck, J. R.; Bondlela, M.; Ye, J.; Cho, S.-D. Tetrahedron Lett. 1999, 40, 5647.
18. Reactions based on the coupling of benzylic electrophiles instead of benzylic stannanes or boronates have been described. For reactions of benzylic bromieds and aryl stannanes, see: (a) Kamlage, S.; Sefkow, M.; Peter, M. G. J. Org. Chem. 1999. 64, 2938.
19. Reactions involving benzylic bromides and aryl stannanes are described in: (b) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
20. Cross-coupling between phenyl-or naphthylbronic acids and benzylic bromies havealso been reported: (c) Chrowdhury, S.; Georghiou, S.; Georghiou, P. E. Tetrahedron Lett. 1999, 75, 7599.
21. (d) Klärner, C.; Greiner, A. Macromol. Rapid Commun. 1998, 19, 605.
22. Garcia Martinez, A.; Osio Barcina, J.; de Fresno Cerezo, A.; Subramanian, L. R. Synlett 1994, 1047.
23. Garcia Martinez, A.; Osio Barcina, J.; Colorado Heras, M. R.; de Fresno Cereno, A. Org. Lett. 2000, 2, 1377.
24. In the meantime, some other examples of Pd(0) cross-coupling reactions of hypervalent tin reagents have been described. For the fluoride-activated reactions of monorganotjins with aryl and vinyl odides and benzylic bromides, see: (a) Fouquet, E.; Pereyre, M.; Rodriguez, A. L. J. Org. Chem. 1997, 62, 5242.
25. 4NF, see:
26. (c) Fugami K.; Ohnuma, S.; Kameyama, M.; Saotome, T.; Kosugi, M. Synlett 1999, 63.
27. For reactions of aryl chlorides with tetraorganotins and CsF, see: (d) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411.
28. Also hypervalent silicon and boron reagents have been employed in Pd(0)-catalyzed cross-coupling reactions. For procedures involving hypervalent silicon compounds, see: (e) Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2137.
29. (f) Mowery, M. E.; deShong, P. J. Org. Chem. 1999, 64, 1684.
30. (g) Mowery, M. R.; DeShong, P. J. Org. Chem. 1999, 64, 3266.
31. (h) Matsuhashi, H.; Asai S.; Hirahayashi, K.; Hatanaka, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jp. 1997, 70, 437.
32. (i) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845.
33. For fluoride-mediated boronic acid cross-coupling reactions, see: (j) Wright, S.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
34. (a) Gingras, M. Tetrahedron Lett. 1991, 32, 7381.
35. (b) Jang, M.; Janzen, A. F. J. Fluorine Chem. 1994, 66, 129.
36. Gingras, M.; Chan, T. H.; Harpp, D. N. J. Org. Chem. 1990, 55, 2078.
37. For a review on the synthesis of biaryls, see: Stanforth, S. P. Tetrahedron 1998, 263.
38. Some procedures for the preparation of diphenylmethanes are described in: (a) Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron Lett. 1998, 38, 6291.
39. (b) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. J. Org. Chem. 1997, 64, 66997.
40. (c) Kim, S.-H.; Rieke, R. D. J. Org. Chem. 1998, 63, 6766.
41. (d) Rottländer, M.; Nochel, P. Tetrahedron Lett. 1997, 38, 1749.
42. (e) Ku, Y.-Y.; Patel, R. R.; Sawichk, D. P. Tetrahedron Lett. 1996, 37, 1949.
43. (f) Yamata, T.; Sakane, N.; Suehiro, K.; Tashiro, M. Org. Prep. Proc. Int. 1991, 23, 617.
44. (a) Garcia Martinez, A.; Subramanian, L. R.; Hanack, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: Chichester, 1995; Vol. 7,
45. (b) Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 55.
46. (a) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
47. (b) Crisp, G. T.; Scott, W. J. Synthesis 1985, 335.
48. Sisido, K.; Takeda, Y.; Kinigawa, Z. J. Am. Chem. Soc. 1961, 83, 583.
49. Liebner, J. E.; Jacobus, J. J. Org. Chem. 1997, 64, 4449.
50. Eisch, J. J. Organometallic Syntheses, vol. 2, Nontransition-Metal Compounds; Academic Press: New York, 1981.