Short syntheses of 8-substituted 8′-[1-(1′-phenylthio)ferrocenyl]-1,1′-binaphthyls from Suzuki coupling reactions. A strategy for generating new chiral ligands and charge-transfer complexes

Journal of Organometallic Chemistry

Volumn 637, Issue 639, 2001, Pages 832-836

  Hua, Duy H ^a   McGill, James W ^a   Ueda, Masato ^a   Stephany, Heidi A ^a  

^a KANSAS STATE UNIVERSITY   (United States)

Author keywords

Charge transfer complexes; Chiral phosphines; Suzuki coupling; Unsymmetrical 8,8 disubstituted 1,1 binaphthyls

Indexed keywords

LATEOLABRAX JAPONICUS;

EID: 0035803685     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)01141-X     Document Type: Article

References (22)

1. Togni A., Hayashi T. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Material Science. 1995;VCH, Weinheim.
2. Togni A., Halterman R.L. Metallocenes. 1998;Wiley, New York, NY.
3. For a recent review of 1,1′-binaphthyl in asymmetric catalysis and new materials, see: Pu L. Chem. Rev. 98:1998;2405.
4. For 2,2′-binaphthalenediyl-substituted ferrocenes: Foxman B.M., Rosenblum M. Organometallics. 12:1993;4805.
5. J.W. McGill, H.-S. Sin, T.X.C. Nguyen, Y. Chen, X. Huang, P. Roach, K. Mijares, D.H. Hua, Chiral 8,8′-Disubstituted 1,1′-Binaphthyls in Asymmetric Catalytic Palladium-Mediated Ring Closure Reactions, 35th Midwest Regional Meeting of the American Chemical Society, St. Louis, MO, USA, 25-28 October, Abstr. No. 56, 2000, p. 85.
6. Fuji K., Sakurai M., Kinoshita T., Kawabata T. Tetrahedron Lett. 39:1998;6323.
7. For reviews of Heck reactions: de Meijere A., Meyer F.E. Angew. Chem. Int. Ed. Engl. 33:1994;2379.
8. A journal issue was dedicated to J. Tsuji and R.F. Heck: J. Organomet. Chem. 576 (1999) 1-318.
9. Miller J.S., Calabrese J.C., Harlow R.L., Dixon D.A., Zhang J.H., Reiff W.M., Chittipeddi S., Selover M.A., Epstein A.J. J. Am. Chem. Soc. 112:1990;5496.
10. For a review: Miller J.S., Epstein A.J. Angew. Chem. Int. Ed. Engl. 33:1994;385.
11. For reviews of Suzuki coupling reactions: N. Miyaura, Advances in Metal-Organic Chemistry, vol. 6, JAI Press Inc., Connecticut, 1998, pp. 187-243.
12. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457.
13. Coupling of ferrocenylboronic acids with phenyl halides: Knapp R., Rehahn M. J. Organomet. Chem. 452:1993;235.
14. Asymmetric oxidation of ferrocenyl sulfides to ferrocenyl sulfoxides has been reported: (a) P. Diter, O. Samuel, S. Taudien, H.B. Kagan, Tetrahedron: Asymmetry 5 (1994) 549;
15. N.M. Lagneau, Y. Chen, P.M. Robben, H.-S. Sin, K. Takasu, J.-S. Chen, P.D. Robinson, D.H. Hua, Tetrahedron 54 (1998) 7301 (and references cited therein).
16. Dyker G. J. Org. Chem. 58:1993;234.
17. House H.O., Koepsell D.G., Campbell W.J. J. Org. Chem. 37:1972;1003.
18. Chieffi A., Comasseto J.V., Snieckus V. Synlett. 2:2000;269.
19. Wright M.E. Organometallics. 9:1990;853.
20. Stille J.K. Pure Appl. Chem. 57:1985;1771.
21. This study is underway and will be reported in due course.
22. Resolution of chiral phosphines via phosphine-borane complexes: Imamoto T., Oshiki T., Onazawa T., Kusumoto T., Sato K. J. Am. Chem. Soc. 112:1990;5244.