Photocatalytic Oxidation of Sulfinates to Vinyl Sulfones with Cyanamide-Functionalised Carbon Nitride

Meyer, Andreas Uwe and Lau, Vincent Wing-hei and Koenig, Burkhard and Lotsch, Bettina V. (2017) Photocatalytic Oxidation of Sulfinates to Vinyl Sulfones with Cyanamide-Functionalised Carbon Nitride. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (15). pp. 2179-2185. ISSN 1434-193X, 1099-0690

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Abstract

The cyanamide-functionalised carbon nitride (NCN-CNx) can be employed as a photo-redox catalyst for the light-induced sulfonylation of alkenes with sulfinate salts, attaining product yields twice those obtained with the non-functionalised counterpart and comparable to those achieved with the benchmark homogeneous photocatalyst Eosin Y. NCN-CNx as a heterogeneous photocatalyst is easily isolatable and can be re-used for this reaction for over three cycles. This photocatalytic reaction can proceed with various sulfinates (aryl-, alkyl- and thiophene-based) and alkenes with electron-donating and -withdrawing groups, obtaining good to excellent product yields. A reductive quenching route was determined to be the likely mechanism for this photocatalyst.

Item Type: Article
Uncontrolled Keywords: LIGHT PHOTOREDOX CATALYSIS; VISIBLE-LIGHT; ORGANIC-SYNTHESIS; HYDROGEN-PRODUCTION; CHEMICAL-SHIFTS; H-2 PRODUCTION; NI CATALYST; EOSIN Y; COMPLEXES; GENERATION; Heterogeneous catalysis; Photocatalysis; Alkenes; Sulfonylation; Reaction mechanisms; Oxidation
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Dec 2018 13:10
Last Modified: 11 Feb 2019 14:06
URI: https://pred.uni-regensburg.de/id/eprint/1029

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