Efficient Pd-catalyzed heterobenzylic cross-coupling using sulfonium salts as substrates and (PhO)3P as a supporting ligand

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2796-2804

  Zhang, Shijie ^a   Marshall, Daniel ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE; PALLADIUM; S (2 FURANYLMETHYL)TETRAMETHYLENESULFONIUM HEXAFLUOROPHOSPHATE; S (2 THIENYLMETHYL)TETRAMETHYLENESULFONIUM HEXAFLUOROPHOSPHATE; S (3 THIENYLMETHYL)TETRAMETHYLENESULFONIUM HEXAFLUOROPHOSPHATE; S (N TERT BUTOXYCARBONYL 2 PYRROLYLMETHYL)TETRAMETHYLENESULFONIUM HEXAFLUOROPHOSPHATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BINDING KINETICS; CATALYSIS; LIGAND BINDING; METAL BINDING; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033574612     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982250s     Document Type: Article

References (46)

1. Kharasch, M. S.; Fields, E. K. J. Am. Chem. Soc. 1941, 63, 2316.
2. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.-i.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
3. Negishi, E.-i. Acc. Chem. Res. 1982, 15, 340.
4. Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551.
5. Farina, V.; Krishnamurthy, V.; Scott, W. J. In Organic Reactions; Paquette, L., Ed.; John Wiley & Sons: New York, 1997; Vol. 50; p 1.
6. Hatanaka, Y.; Hiyama, T. SynLett 1991, 845.
7. Mitchell, T. N. Synthesis 1992, 803.
8. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
9. Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054.
10. Ahman, J.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6363.
11. Wolfe, J. P.; Ahman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367.
12. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694.
13. Mann, G.; Hartwig, J. F.; Driver, f. M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
14. Baranano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
15. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
16. Miyaura, N.; Yano, T.; Suzuki, A. Tetrahedron Lett. 1980, 21, 2865.
17. Vanasselt, R.; Elsevier: C. J. Organometallics 1994, 13, 1972.
18. Lipshutz, B. H.; Bulow, G.; Lowe, R. F.; Stevens, K. L. J. Am. Chem. Soc. 1996, 118, 5512.
19. Lipshutz, B. H.; Bulow, G.; Lowe, R. F.; Stevens, K. L. Tetrahedron 1996, 52, 7265.
20. Srogl, J.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1997, 119, 12376.
21. Divald, S.; Chun, M. C.; Joullié, M. M. J. Org. Chem. 1976, 41, 2835.
22. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
23. Farina, V.; Roth, G. P. Tetrahedron Lett. 1991, 32, 4243.
24. Flowers, W. T.; Freitas, A. M.; Holt, G.; Purkiss, S. C. J. Chem. Soc., Perkin Trans. 1 1981, 1119.
25. Kim, S.; Park, J. H.; Kim, Y. G.; Lee, J. M. J. Chem. Soc., Chem. Commun. 1993, 1188.
26. Rahman, M. M.; Liu, H. Y.; Eriks, K.; Giering, W. P. Organometallics 1989, 8, 1.
27. Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
28. Smith, A. B., III.; Ott, G. R. J. Am. Chem. Soc. 1998, 120, 3935.
29. Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 5; p 1.
30. Liebeskind, L. S.; Foster, B. F. J. Am. Chem. Soc. 1990, 112, 8612.
31. Liebeskind, L. S.; Riesinger, S. W. J. Org. Chem. 1993, 58, 408.
32. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
33. The organostannane homocoupling product can form if there ia a slow transmetalation of the stannane to the palladium intermediate (formed by oxidative addition of the sulfonium salt to Pd). A related process was described: Koo, S.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 111, 3389.
34. Piers, E.; McEachern, E. J.; Gladstone, P. L. Can. J. Chem. 1997, 75, 694.
35. Piers, E.; Wong, T. J. Org. Chem. 1993, 58, 3609.
36. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
37. Negishi, E.; Ay, M.; Gulevich, Y. V.; Noda, Y. Tetrahedron Lett. 1993, 34, 1437.
38. Frontier Scientific Inc., P.O. Box 31, Logan, UT 84323-0031.
39. Farina, V. J. Org. Chem. 1991, 56, 4985.
40. Saa, J. M.; Martorell, G. J. Org. Chem. 1993, 58, 1963.
41. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4371.
42. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129.
43. Mascarenas, J. L.; Garcia, A. M.; Castedo, L.; Mourino, A. Tetrahedron Lett. 1992, 33, 7589.
44. Stang, P. J.; Tykwinski, R.; Zhdankin, V. V. J. Heterocycl. Chem. 1992, 29, 815.
45. Davies, H. M. L.; Matasi, J. J.; Ahmed, G. J. Org. Chem. 1996, 61, 2305.
46. Ireland, R. E.; Thaisrinongs, S.; Dussalt, P. H. J. Am. Chem. Soc. 1988, 110, 5768.