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Issue 3, 2014
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From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual SNAr via thiolate displacement?

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Abstract

Treatment of meso 2-ethylhexyl-3-mercaptopropionate substituted porphyrins with base at room temperature generated a porphyrin thiolate anion which in situ reacted in a nucleophilic aromatic substitution (SNAr) reaction with remaining thioether derivative. This reaction yielded S-linked bisporphyrins in good yields, with mechanistic insight obtained via displacement reactions. Additionally, SNAr of the thioether chain was achieved using S- and organolithium nucleophiles.

Graphical abstract: From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual SNAr via thiolate displacement?

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Publication details

The article was received on 06 Sep 2013, accepted on 11 Nov 2013 and first published on 11 Nov 2013


Article type: Communication
DOI: 10.1039/C3CC46828C
Citation: Chem. Commun., 2014,50, 353-355
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    From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual SNAr via thiolate displacement?

    A. A. Ryan, S. Plunkett, A. Casey, T. McCabe and M. O. Senge, Chem. Commun., 2014, 50, 353
    DOI: 10.1039/C3CC46828C

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