Palladium-catalyzed homocoupling of organostannanes

Synthetic Communications

Volumn 27, Issue 4, 1997, Pages 641-646

  Kang, Suk Ku ^a   Namkoong, Eun Young ^a   Yamaguchi, Tokutaro ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BIPHENYL; FURAN DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030943247     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708003337     Document Type: Article

References (12)

1. (a) For reviews see: (a) Mitchell, T. N. Synthesis 1992, 803-815.
2. (b) Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
3. Kanemoto, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Chem. Lett. 1987, 5-6.
4. 2COR (R = Me) was used: Shinya, Y.; Kariya, M.; Kikukawa, K., 10th International Conference on Organic Synthesis, Bangalore, India, December 11-16, 1994; poster number, P-THU-90.
5. Liebeskind, L. S.; Riesinger, S.W. Tetrahedron Lett. 1991, 32, 5681-5682.
6. 2. See, Boons, G-J.; Entwistle, D.A.; Ley, S. V.; Woods, M. Tetrahedron Lett. 1993, 34, 5649-5652.
7. Tolstikov, G. A.; Miftakhov, M. S.; Danilova, N. A.; Velder, Ya. L.; Spirikhin, L. Y. Synthesis 1989, 633-634.
8. In the Stille coupling reaction of olefinic stannanes considerable amounts of stannane homocoupling were encountered though mechanistically unexplainable. See, (a) Friesen, R. W.; Sturino, C. F. J. Org. Chem. 1990, 55, 2572-2574. (b) Dubois, E.; Beau, J. M. Tetrahedron Lett. 1990, 31, 5165-5168.
9. In the Stille coupling reaction of olefinic stannanes considerable amounts of stannane homocoupling were encountered though mechanistically unexplainable. See, (a) Friesen, R. W.; Sturino, C. F. J. Org. Chem. 1990, 55, 2572-2574. (b) Dubois, E.; Beau, J. M. Tetrahedron Lett. 1990, 31, 5165-5168.
10. In the Stille coupling, the use of triphenylarsine as ligand accelerates the rates. See, Farina, V.; Krishinan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
11. Presumably, 1, 2-dichloroethane regenerates Pd(II) by oxidation of Pd(0) in catalytic cycle if double transmetallation followed by reductive elimination is assumed. For the use of 1, 2-dichloroethane as Pd(0) reoxidant, see, Ait-Mohand, S.; Henin, F.; Muzart, J. Tetrahedron Lett. 1995, 36, 2473-2476.
12. Larock, R. C.; Bernhardt, J. C. J. Org. Chem. 1977, 42, 1680-1684.