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Rational Synthesis of 2-Bromoporphyrins and 2,12-Dibromoporphyrins
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
2017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 23, p. 12908-12913Article in journal (Refereed) Published
Abstract [en]

Bromoporphyrins were prepared by the metal-mediated self-condensation of brominated 1-formyldipyrromethanes. Depending on the conditions, Mg(II)-2,12-dibromoporphyrin and Mg(II)-2-bromoporphyrin could be obtained in up to 11% and 17% isolated yield, respectively. Zn(II) was also a viable templating metal. The positions of the bromine substituents were confirmed by 2D-NMR spectroscopic analysis and the X-ray crystal structure of a derivative. Suzuki and Sonogashira reactions of the bromoporphyrins yielded 2-substituted or 2,12-disubstituted porphyrins with red-shifted absorption and emission spectra. This method provides access to the minimalist core of beta-mono- and beta,beta'-disubstituted porphyrins from readily available starting materials.

Place, publisher, year, edition, pages
2017. Vol. 82, no 23, p. 12908-12913
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-343907DOI: 10.1021/acs.joc.7b02404ISI: 000417342300100OAI: oai:DiVA.org:uu-343907DiVA, id: diva2:1187148
Funder
Swedish Research Council, 2013-4655Available from: 2018-03-02 Created: 2018-03-02 Last updated: 2018-03-08Bibliographically approved

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Bornhof, Anna-BeaXiong, RuishengBorbas, K. Eszter

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