Rapid microwave-assisted Suzuki coupling on solid-phase

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8219-8222

  Larhed, Mats ^a   Lindeberg, Gunnar ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; MICROWAVE RADIATION; REACTION ANALYSIS;

LATEOLABRAX JAPONICUS;

EID: 0007404508     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01872-2     Document Type: Article

References (34)

1. 1. For recent reviews, see: a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527,
2. b) Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17,
3. c) DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114,
4. d) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. ibid. 1996, 29, 123,
5. e) Ellman, J. A. ibid. 1996, 29, 132,
6. f) Gordon, E. M.; Gallop, M. A.; Patel, D. V. ibid. 1996, 29, 144,
7. g) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555,
8. h) Lowe, G. Chem. Soc. Rev. 1995, 24, 309.
9. 2. Frenette, R.; Friesen, R. W. Tetrahedron Lett. 1994, 35, 9177.
10. 3. a) Boojamra, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742,
11. b) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171.
12. 4. Goff, D. A.; Zuckermann, R. N. J. Org. Chem. 1995, 60, 5744.
13. 5. Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.
14. 6. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169.
15. 7. a) Strauss, C. R.; Trainor, R. W. Aust. J. Chem. 1995, 48, 1665,
16. b) Caddick, S. Tetrahedron 1995, 51, 10403,
17. c) Loupy, A.; Bram, G.; Sansoulet, J. New J. Chem. 1992, 16, 233,
18. d) Abramovitch, R. A. Org. Prep. Proc. Int. 1991, 23, 683,
19. e) Mingos, D. M. P.; Baghurst, D. R. Chem. Soc. Rev. 1991, 20, 1.
20. 8. For reviews on the Suzuki reaction see: a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457,
21. b) Martin, A. R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221.
22. 9. 90 μm Fmoc TentaGel S RAM-resin (S30 023, 0.23 mmol/g capacity) purchased from Rapp Polymere.
23. 10. The 4-halobenzoic acids (4 eq.) were coupled to deprotected resin using 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyl-uronium hexafluorophosphate (HBTU, 4 eq.) and DIEA (8 eq.) for 2 h. Remaining amino groups were then capped by acetylation
24. 11. Microwave heating was carried out with a MicroWell 10 single-mode microwave cavity producing constant irradiation (2450 MHz), Labwell AB, Östra Ågatan 51 A, S-753 22 Uppsala, Sweden, e-mail: Soren Nygren@Labwell.se CAUTION! Suitable precautions should always be taken with reactions carried out in closed vessels due to the risk of explosion. 12. Release of PEG was observed also from the non-functionalised resin. 150 mg Fmoc TentaGel S RAM-resin was deprotected with 20% piperidine/DMF and was treated thereafter with 99% aq. TFA for 1h (cleavage conditions). This procedure afforded 2.8 mg crude PEG.
25. 3 as ligand in Stille reactions is recommended by Farina. a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585. Stille reactions on support-bound aryl halides have recently been reported:
26. b) Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613,
27. c) Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523.
28. 1H-NMR.
29. 1H-NMR) for the released PEG in the cleavage step.
30. 1H-NMR spectra (DMSO-D6) as well as appropriate ion identification by mass spectrometry (EI or PDMS) and had purity >95% by GC/MS.
31. 17. The reactions were performed in heavy-walled pyrex tubes (8 ml, 1=150 mm) equipped with screw caps and silicon septa. The reaction volume filled not more than 1 / 5th of the total volume of the tube, thereby allowing head space for pressure build-up during the microwave treatment.
32. 18. DME was introduced as solvent in the Suzuki reaction by Gronowitz. Gronowitz, S.; Bobosik, V.; Lawitz, K. Chem. Scr. 1984, 23, 120.
33. 19. a) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
34. b) Backes, B. J. Unpublished observation.