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Synthesis 2002(16): 2365-2372
DOI: 10.1055/s-2002-35240
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Coupling Reactions of Paramagnetic Vinyl Halides

Tamás Kálaia, Mária Baloga, József Jekőb, Wayne. L. Hubbellc, Kálmán Hideg*a
a Institute of Organic and Medicinal Chemistry, University of Pécs, 7643 Pécs, P. O. Box 99, Hungary
Fax: +36(72)536219; e-Mail: KHIDEG@main.pote.hu;
b ICN, Hungary, 4440 Tiszavasvári, P. O. Box 1, Hungary
c Jules Stein Eye Institute and Department of Chemistry and Biochemistry, UCLA, Los Angeles, CA 90095-7008, USA
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Publication History

Received 19 June 2002
Publication Date:
04 November 2002 (online)

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Abstract

Suzuki, Heck and Sonogishira coupling reactions of paramagnetic vinyl bromides 1-6 gave monofunctional (7a,b), homobifunctional (8a,b, 24), and heterobifunctional pyrroline nitroxides (9-19, 31) under mild conditions in a one-step reaction. From these compounds thiol-specific spin labels 26 and 28 and pyrroline nitroxide annulated heterocycles 30 and 32 were synthesized. The ethynyl derivative of pyrroline nitroxide 33 also can be used as an acetylene reactant in Larock indole synthesis to give the paramagnetic indole derivative 36.

Key words

alkynes - free radical - Suzuki reaction - heterocycles - palladium