Cross-coupling reaction of organostannanes with aryl halides catalyzed by nickeltriphenylphosphine or nickel-lithium halide complex

Synthesis

Volumn , Issue 10, 1998, Pages 1544-1549

  Shirakawa, Eiji ^a,b   Yamasaki, Kenji ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Aryl chloride; Cross coupling; Ligand effect; Nickel; Organostannane

Indexed keywords

CHLORIDE; HALIDE; IODOBENZENE; LITHIUM DERIVATIVE; NICKEL COMPLEX; ORGANOTIN COMPOUND; PHOSPHINE DERIVATIVE; TRIBUTYLTIN; VINYL DERIVATIVE;

CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REVIEW;

EID: 0031786432     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2172     Document Type: Review

References (42)

1. Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Ed.; Pergamon: New York, 1995; Vol. 12, Chapter 3.4; p 161.
2. For reviews, see: Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
3. Mitchell, T. N. Synthesis 1992, 803.
4. Ritter, K. Synthesis 1993, 735.
5. For a review, see: Farina, V. Pure Appl. Chem. 1996, 68, 73.
6. We reported another approach to an active catalyst for this coupling reaction. Shirakawa, E.; Yoshida, H.; Takaya, H. Tetrahedron Lett. 1997, 38, 5177.
7. In a series of pioneering works by Migita, Kosugi and their coworkers concerning the transition metal-catalyzed coupling of organostannanes, a rhodium complex was used as a catalyst. Kosugi, M.; Shimizu Y.; Migita, T. J. Organomet. Chem. 1977, 129, C36.
8. Nickel catalysts are widely used for the cross-coupling reaction of Grignard reagents. See: Tamao, K.; Sumitani K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
9. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Soc. Chem. Jpn. 1976, 49, 1958.
10. Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895.
11. A part of this study is already reported. Shirakawa, E.; Yamasaki, K.; Hiyama, T. J. Chem. Soc., Perkin Trans. 1 1997, 2449.
12. Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
13. For a review of the transformation of chloroarene catalyzed by transition metal complexes, see: Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
14. 3): for 1a: δ= 12.64; 3a: δ= 13.10.
15. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
16. An example of phosphine inhibition in the palladium-catalyzed coupling of aryl halides with organostannanes is seen in reference 12. Phosphine inhibition is observed also in the coupling of arylboronic acid, see: Wallow, T. I.; Novak, B. M. J. Org. Chem. 1994, 59, 5034.
17. 3): for 1a: δ= 12.64; 1b: δ= 12.87; 1c: δ= 13.03; 1d: δ= 12.99, 2.95; 3a: δ= 13.10; 3b: δ= 13.30; 3c: δ= 12.85.
18. A Ni(0) complex coordinated by 1,1′-(diphenylphosphino)ferrocene was used effectively as a catalyst for the cross-coupling reaction of arylboronic acid with aryl chlorides. Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 37, 2993.
19. Saito, S.; Oh-tani, O.; Miyaura, N. J. Org. Chem. 1997, 62, 8024.
20. A similar competitive experiment in the palladium-catalyzed coupling of a vinylstannane with p- and o-(trifluoromethanesulfonyl)acetophenone gave the para derivative as the main product in a ratio of 73 to 27. Farina, V.; Baker, S. R.; Benigni, D. A.; Hauck, S. I.; Sapino, Jr., C. J. Org. Chem. 1990, 55, 5833.
21. Seyferth, D.; Stone, F. G. A. J. Am. Chem. Soc. 1957, 79, 515.
22. Logue, M. W.; Teng, K. J. Org. Chem. 1982, 47, 2549.
23. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129.
24. Groh, B. L. Tetrahedron Lett. 1991, 32, 7647.
25. Jones, K.; Lappert, M. F. Proc. Chem. Soc. 1964, 22.
26. Allen, D. W.; Tayler, B. F. J. Chem. Soc., Dalton Trans. 1982, 51.
27. Baldwin, J. E.; Kapecki, J. A. J. Am. Chem. Soc. 1970, 92, 4869.
28. Benedetto, S. D.; Consiglio, G. Helv. Chim. Acta. 1997, 80, 2204.
29. Kiplinger, J. L.; King, M. A.; Fechtenkötter, A.; Arif, A. M.; Richmond, T. G. Organometallics 1996, 15, 5292.
30. 1 1991, 1099.
31. Efange, S. M. N.; Michelson, R. H.; Dutta, A. K.; Parsons, S. M. J. Med. Chem. 1991, 34, 2638.
32. Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716.
33. Tsubakiyama, K.; Yamamoto, M.; Nishijima, Y. J. Polym. Sci., Part A: Polym. Chem. 1988, 26, 1231.
34. Brown, R. F. C.; Eastwood, F. W.; Chaichit, N.; Gatehouse, B. M.; Pfeiffer, J. M.; Woodroffe, D. Aust. J. Chem. 1981, 34, 1467.
35. Parrinello, G.; Deschenaux, R.; Stille, J. K. J. Org. Chem. 1986, 57, 4189.
36. Ishizone, T.; Sugiyama, K.; Hirao, A.; Nakahama, S. Macromolecules 1993, 26, 3009.
37. Echavarren, A, M.; Stille, J, K. J. Am. Chem. Soc. 1987, 109, 5478.
38. Hollywood, F.; Suschitzky, H. Synthesis 1982, 8, 662.
39. Tzeng, Y. L.; Yang, P. F.; Mei, T. M.; Yuan, T. M.; Yu, C. C.; Luh, T. Y. J. Org. Chem. 1991, 56, 5289.
40. Copper, M. K.; Yaniuk, D. W. J. Organomet. Chem. 1981, 221, 231.
41. Hamer, G. K.; Peat, I. R.; Reynolds, W. F. Can. J. Chem. 1973, 51, 897.
42. Hirao, A.; Kato, K.; Nakahama, S. Macromolecules 1992, 25, 535.