Palladium-Catalyzed Cross-Coupling Reactions of Paramagnetic Vinyl Bromides and Paramagnetic Boronic Acids

Tamás Kálai; József Jekő; Zoltán Berente; Kálmán Hideg

doi:10.1055/s-2006-926279

PAPER

Palladium-Catalyzed Cross-Coupling Reactions of Paramagnetic Vinyl Bromides and Paramagnetic Boronic Acids

Tamás Kálai^a, József Jekő^b, Zoltán Berente^c, Kálmán Hideg*^a
^a Institute of Organic and Medicinal Chemistry, University of Pécs, P. O. Box 99, 7602 Pécs, Hungary
Fax: +36(72)536219; e-Mail: kalman.hideg@aok.pte.hu;
^b ICN, Hungary, P.O. Box 1, 4440 Tiszavasvári, Hungary
^c Institute of Biochemistry and Medical Chemistry, University of Pécs, P. O. Box 99, 7602 Pécs, Hungary

Abstract

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Abstract

Suzuki reactions are utilized for the synthesis of heterobifunctional cross-linking reagents (thiol- or aminospecific and photoactivatable), polyaromatics (such as phenanthrene) and heterocycles (such as coumarin and quinoline), anellated nitroxides and paramagnetic, biologically active molecules (such as cis-stilbene and nicotinamide). Furthermore, the synthesis of new vinyl and allyl boronic acid esters is also reported.

Key words

boron - cross-coupling - free radicals - heterocycles - palladium

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References

1 Hubbell WL. Altenbach C. Hubbell CM. Khorana HG. Adv. Protein. Chem. 2003, 63: 243

2 Nerbouh N. Bobbit JM. Brückner C. Org. Prep. Proced. Int. 2004, 36: 1

3 Bilski P. Hideg K. Kálai T. Bilska MA. Chignell CF. Free Radical Biol. Med. 2003, 34: 489

4 Magnetic Properties of Organic Materials Lahti MP. Marcell Dekker Inc.; New York: 1999.

5 Shen J. Bottle S. Khan N. Grinberg O. Reid D. Micallef A. Swartz H. Appl. Magn. Reson. 2002, 22: 357

6 Braslau R. Chaplinski V. Goodson P. J. Org. Chem. 1998, 63: 9857

7 Kálai T. Szabó Z. Jekő J. Hideg K. Org. Prep. Proced. Int. 1996, 28: 289

8 Kálai T. Kulcsár G. Õsz E. Jekő J. Sümegi B. Hideg K. ARKIVOC 2004, (vii): 266

9 Hideg K. Hankovszky HO. Halász HA. Sohár P. J. Chem. Soc., Perkin Trans. 1 1988, 2905

10 Kálai T. Balog M. Jekő J. Hideg K. Synthesis 1999, 973

11 Kálai T. Balog M. Jekő J. Hubbell WL. Hideg K. Synthesis 2002, 2365

12 Suzuki A. Brown HC. Organic Synthesis via Boranes Vol. 3: Aldrich Chemical Company Inc.; Milwaukee: 2003.

13 Zhdanov RI. In Bioactive Spin Labels Zhdanov RI. Springer-Verlag; Berlin: 1992. p.23-82

14 Barton HR. Bashiardes G. Fourrey J.-L. Tetrahedron 1988, 44: 147

15 Kálai T. Jekő J. Hideg K. Tetrahedron Lett. 2004, 45: 8395

16 Berliner LJ. Grünwald J. Hankovszky HO. Hideg K. Anal. Biochem. 1982, 119: 450

17 Lösel RM. Philipp R. Kálai T. Hideg K. Trommer WE. Bioconjugate Chem. 1999, 10: 578

18 Mátyus P. Maes BUW. Riedl Z. Hajós G. Lemiére GLF. Tapolcsányi P. Monsieurs K. Éliás O. Dommisse RA. Krajsovszky G. Synlett 2004, 1123

19 Sampathkumar NM. Kumar NV. Rajendran SP. Synth. Commun. 2004, 34: 2019

20 Gug F. Blondel M. Deaban N. Bouaziz S. Vierfond J.-M. Galons H. Tetrahedron Lett. 2005, 46: 3725

21 Keana JFW. Hideg K. Birrell GB. Hankovszky HO. Ferguson G. Parvez M. Can. J. Chem. 1982, 60: 1439

22 Clayden J. Organolithiums: Selectivity for Synthesis Elsevier; Oxford: 2002.

23 Chaumel H. Le Drian C. Defoin A. Synthesis 2002, 757

24 Wegner HA. Scott TA. de Meijere A. J. Org. Chem. 2003, 68: 883

25 Shapiro AB. Dimitriev PI. Bull. Acad. Sci. USSR, Div. Chemical Sci. 1981, 138

26 Ishiyama T. Murata M. Miyaura N. J. Org. Chem. 1995, 60: 7508

27 Liu X. Synlett 2003, 2442

28 Wang Z. Meng X.-J. Kabalka GW. Tetrahedron Lett. 1991, 32: 1945

29 Barluenga J. Fananas JF. Snaz R. Ignacio JM. Eur. J. Org. Chem. 2003, 771

30 Hideg K. Csekõ J. Hankovszky HO. Sohár P. Can. J. Chem. 1986, 64: 1482

31 Ishiyama T. Matsuda N. Miyaura N. Suzuki A. J. Am. Chem. Soc. 1993, 115: 11018

32 Lion CJ. Matthews CS. Stevens MFG. Westwell AD. J. Med. Chem. 2005, 48: 1292

33 Kálai T. Balog M. Jekő J. Hideg K. Synthesis 1998, 1476