The Suzuki-Miyaura cross coupling reactions on solid support. Link to solution phase directed ortho metalation. The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4179-4182

  Chamoin, S ^a   Houldsworth, S ^a   Kruse, C G ^b   Bakker, W Iwema ^b   Snieckus, V ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

^b Solvay Pharmaceuticals Inc   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HYDROLYSIS;

LATEOLABRAX JAPONICUS;

EID: 0032508079     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00779-5     Document Type: Article

References (13)

1. 1. Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175.
2. 2. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
3. For recent cases on SS, see a) Backes, B.J.; Ellman, J.A. J. Am. Chem. Soc. 1994, 116, 11171.
4. b) Piettre, S.R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197.
5. c) Ruhland, B.; Bombrun, A.; Gallop, M.A. J. Org. Chem. 1997, 62, 7820.
6. 3. Snieckus, V. Chem. Rev. 1990, 90, 879; Snieckus, V. In Chemical Synthesis: Gnosis to Prognosis, Chatgilialoglu, C.; Snieckus, V., Eds.; NATO ASI Series, Kluwer Academic Publishers: The Netherlands, 1996, Series E: Applied Sciences, Vol. 320, p 191.
7. 3. Snieckus, V. Chem. Rev. 1990, 90, 879; Snieckus, V. In Chemical Synthesis: Gnosis to Prognosis, Chatgilialoglu, C.; Snieckus, V., Eds.; NATO ASI Series, Kluwer Academic Publishers: The Netherlands, 1996, Series E: Applied Sciences, Vol. 320, p 191.
8. 4. Leznoff, C.C.; Wong, J.Y. Can. J. Chem. 1973, 51, 3756; Leznoff, C.C.; Sywanyk, W. J. Org. Chem. 1977, 42, 3203.
9. 4. Leznoff, C.C.; Wong, J.Y. Can. J. Chem. 1973, 51, 3756; Leznoff, C.C.; Sywanyk, W. J. Org. Chem. 1977, 42, 3203.
10. 5. The loading of the bromo-benzaldehydes were approximatly 0.6 mequiv/g in each case.
11. 1H NMR.
12. 7. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D.C. Tetrahedron 1997, 53, 5643.
13. 8. All new compounds show satisfactory spectroscopic (NMR, HRMS) and analytical data.