Pd- mediated C-C bond formation with olefins and acetylenes on solid support: A scope and limitations study

Synlett

Volumn , Issue 6, 1998, Pages 676-678

  Berteina, Sabine ^a   Wendeborn, Sebastian ^a   Brill, Wolfgang K D ^a   De Mesmaeker, Alain ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002477156     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-22662     Document Type: Article

References (17)

1. Wendeborn, S.; Berteina, S.; Brill, W. K.-D; De Mesmaeker, A. Synlett 1998, 671.
2. a) de Meijere, A; Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
3. b) Heck, R.F. Palladium Reagents in Organic Synthesis; Academic Press, 1985.
4. c) Dieck, H.A.; Heck, F.R. J. Organometallic Chem. 1975, 93, 259.
5. a) Yu, K.-L.; Deshpande, M.S.; Dolatrai, M.V. Tetrahedron Lett. 1994, 35, 8919.
6. b) Young, K.-Y.; Nelson, J.C.; Moore, J.S. J. Am. Chem. Soc. 1994, 116, 10841.
7. c) Fagnola, M.C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307.
8. d) Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311.
9. Double couplings imply complete removal of all reagents and side products through washing of the resin before submitting it under identical coupling conditions for a second time. If the washing step is avoided, no significantly increased yields were observed, presumably due to accumulation of catalyst poisoning side products.
10. 1H-NMR (400 MHz).
11. Takagi, K.; Sasaki, K.; Sakakibara, Y. Bull. Chem. Soc. Jpn. 1991, 64, 1118.
12. a) Heck, R.F. Org. React. 1982, 27, 345.
13. b) Heck, R.F. Comprehensive Organic Synthesis, Trost, B.M. and Fleming, I.; Eds; Pergamon Press: New York, 1991, Vol. 4. pp 833.
14. For previous Heck reactions on solid phase see: reference 3a) and a) Hiroshige, M.; Hauske, J.R.; Zhou, P. Tetrahedron Lett. 1995, 36, 4567.
15. For intramolecular Heck reactions on the solid phase see: b) Goff, D.A.; Zuckermann, R.N. J. Org. Chem. 1995, 60, 5748.
16. c) Yun W.; Mohan, R. Tetrahedron Lett. 1996, 37, 7189.
17. 1H-NMR (400 MHz).