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Synthesis 2017; 49(16): 3740-3748
DOI: 10.1055/s-0036-1589034
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium- and/or Copper-Catalyzed Cross-Coupling Reactions of Paramagnetic Vinyl Bromides and Iodides

Györgyi Úr
a   Institute of Organic and Medicinal Chemistry, University of Pécs, Szigeti st. 12, 7624 Pécs, Hungary
,
Gergely Gulyás Fekete
b   Institute of Pharmacognosy, University of Pécs, Rókus st. 2, 7624 Pécs, Hungary
,
József Jekő
c   Department of Chemistry, University of Nyíregyháza, Sóstói st. 31/B, 4440 Nyíregyháza, Hungary
,
Kálmán Hideg
a   Institute of Organic and Medicinal Chemistry, University of Pécs, Szigeti st. 12, 7624 Pécs, Hungary
,
Tamás Kálai*
a   Institute of Organic and Medicinal Chemistry, University of Pécs, Szigeti st. 12, 7624 Pécs, Hungary
d   Szentágothai Research Center, Ifjúság st. 20, 7624 Pécs, Hungary   Email: tamas.kalai@aok.pte.hu
› Author AffiliationsThis work was supported by the National Research Development and Innovation Office (OTKA 104956) and GINOP 2.3.2-15-2016-00049.
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Publication History

Received: 29 January 2017

Accepted after revision: 20 April 2017

Publication Date:
15 May 2017 (online)

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Dedicated to the memory of Prof. Tamás Patonay

Abstract

A series of new 3-substituted-4-iodo-(2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yl)oxidanyl compounds is synthesized to achieve NH2- and SH-specific spin labels. The new vinyl iodides are tested in Sonogashira and Buchwald–Hartwig cross-coupling reactions to produce a paramagnetic β-amino acid ester, pyrroline nitroxide-condensed­ heterocycles, including a paramagnetic α,α′-dipyridyl ligand and a spin-labeled sulfonamide.

Key words

cross-coupling reactions - free radicals - pyridines - pyrimidines - sulfonamides

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    Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589034.
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