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Issue 4, 2018
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Eosin Y photoredox catalyzed net redox neutral reaction for regiospecific annulation to 3-sulfonylindoles via anion oxidation of sodium sulfinate salts

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Abstract

An eosin Y photoredox catalyzed net redox neutral process for 3-sulfonylindoles via the anionic oxidation of sodium sulfinate salts and its radical cascade cyclization with 2-alkynyl-azidoarenes was developed with visible light as a mediator. The reaction offers metal and oxidant/reductant free, visible light mediated vicinal sulfonamination of alkynes to 2-aryl/alkyl-3-sulfonylindoles and proceeds via the generation of a sulfur-centered radical through direct oxidation of the sulfinate anion by an excited photocatalyst with a reductive quenching cycle. The mild conditions, use of an organic dye as photo-catalyst, bench stability and easily accessible starting materials make the present approach green and attractive.

Graphical abstract: Eosin Y photoredox catalyzed net redox neutral reaction for regiospecific annulation to 3-sulfonylindoles via anion oxidation of sodium sulfinate salts

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Publication details

The article was received on 02 Dec 2017, accepted on 21 Dec 2017 and first published on 21 Dec 2017


Article type: Communication
DOI: 10.1039/C7OB02977B
Citation: Org. Biomol. Chem., 2018,16, 536-540
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    Eosin Y photoredox catalyzed net redox neutral reaction for regiospecific annulation to 3-sulfonylindoles via anion oxidation of sodium sulfinate salts

    R. S. Rohokale, S. D. Tambe and U. A. Kshirsagar, Org. Biomol. Chem., 2018, 16, 536
    DOI: 10.1039/C7OB02977B

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