1702
W. Solodenko et al.
LETTER
within one week to yield the coupling product in 93%
Acknowledgment
isolated yield.
We are indebted to the Fonds der Chemischen Industrie for financi-
al support. We thank Ute Kluge and Uwe Reinecker from Solvay
Pharmaceuticals Research Laboratories for technical assistance.
(7) (a) de Vries, A. H. M.; Parlevliet, F. J.; Schmieder-van de
Vondervoort, L.; Mommers, J. H. M.; Henderickx, H. J. W.;
Walet, M. A. M.; De Vries, J. G. Adv. Synth. Catal. 2002,
344, 996. (b) de Vries, A. H. M.; Mulders, J. M. C. A.;
Mommers, J. H. M.; Henderickx, H. J. W.; De Vries, J. G.
Org. Lett. 2003, 5, 3285.
References
(8) Reviews on microwave-assisted synthesis: (a) Kuhnert, N.
Angew. Chem. Int. Ed. 2002, 41, 1863. (b) Perreux, L.;
Loupy, A. Tetrahedron 2001, 57, 9199. (c) Lew, A.;
Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb.
Chem. 2002, 4, 95. (d) Kappe, C. O. Curr. Opin. Chem.
Biol. 2002, 6, 314. (e) Larhed, M.; Hallberg, A. Drug
Discovery Today 2001, 6, 406. (f) Krstenansky, J. F.;
Cotterill, I. Curr. Opin. Drug Disc. Dev. 2000, 3, 451.
(9) (a) Kabza, K. G.; Chapados, B. R.; Gestwicki, J. E.;
McGrath, J. L. J. Org. Chem. 2000, 65, 1210.
(b) Buchmeiser, M. R.; Lubbad, S.; Mayr, M.; Wurst, K.
Inorg Chim Acta 2003, 345, 145.
(10) Yields of homo-coupled products were below 5%.
(11) Leadbeater, N. E.; Marco, M. Angew. Chem. Int. Ed. 2003,
42, 1407.
(12) Schön, U.; Messinger, J.; Glinschert, W.; Stodenko, W.;
Kirschning, A. Microwave-assisted Suzuki-Miyaura
couplings with an insoluble pyridineoxine Pd precatalyst.
Cambridge Healthtech Institute. Presented at the 11th
Advancing Library Design and Organic Synthesis
Conference, La Jolla, CA, February 2004.
(13) (a) Tulloch, A. A. D.; Winston, S.; Danopoulous, A. A.;
Eastham, G.; Husthouse, M. B. J. Chem. Soc., Dalton Trans.
2003, 699. (b) Nájera, C.; Gil-Moltó, J.; Karlström, S.;
Falvello, L. R. Org. Lett. 2003, 5, 1451.
(1) Onoue, H.; Minami, K.; Nakagawa, K. Bull. Chem. Soc. Jpn.
1970, 43, 3480.
(2) (a) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett.
2000, 2, 1823. (b) Alonso, D. A.; Nájera, C.; Pacheco, M. C.
Adv. Synth. Catal. 2002, 344, 172. (c) Alonso, D. A.;
Nájera, C.; Pacheco, M. C. J. Org. Chem. 2002, 67, 5588.
(d) Botella, L.; Nájera, C. Angew. Chem. Int. Ed. 2002, 41,
179. (e) Botella, L.; Nájera, C. J. Organomet. Chem. 2002,
663, 46. (f) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Adv.
Synth. Catal. 2003, 345, 1146.
(3) Reviews on immobilized precatalysts: (a) Solodenko, W.;
Frenzel, T.; Kirschning, A. In Polymeric Materials in
Organic Synthesis and Catalysis; Buchmeiser, M. R., Ed.;
Wiley-VCH: Weinheim, 2003, 201–240. (b) Clapham, B.;
Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637.
(c) Gladysz, J. A. Chem. Rev. 2002, 102, 3215.
(d) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev.
2002, 102, 3275.
(4) (a) Baleizão, C.; Corma, A.; García, H.; Leyva, A. Chem.
Commun. 2003, 606. (b) Baleizão, C.; Corma, A.; García,
H.; Leyva, A. J. Org. Chem. 2004, 69, 439.
(5) The EmrysTM Optimizer from Personal Chemistry was used
for all experiments described here.
(6) The Suzuki-Miyaura reaction (according to Scheme 2)
could be repeated at room temperature and was completed
Synlett 2004, No. 10, 1699–1702 © Thieme Stuttgart · New York