Sulfoximidations of Benzylic C−H bonds by Photocatalysis

An efficient photocatalytic functionalization of compounds with benzylic C−H bonds by sulfoximidation in visible light is described. The mild reaction conditions allow the use of a broad array of substrates, including diarylmethane, alkyl arenes, arylacetonitrile, 2‐arylacetate, and alkynyl aryl met...

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Veröffentlicht in:Angewandte Chemie International Edition 2018-05, Vol.57 (20), p.5863-5866
Hauptverfasser: Wang, Han, Zhang, Duo, Bolm, Carsten
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient photocatalytic functionalization of compounds with benzylic C−H bonds by sulfoximidation in visible light is described. The mild reaction conditions allow the use of a broad array of substrates, including diarylmethane, alkyl arenes, arylacetonitrile, 2‐arylacetate, and alkynyl aryl methanes. The sulfoximidation process is highly chemoselective and leads to the corresponding sulfoximines in generally good yields. Mechanistic investigations suggested the intermediacy of sulfoximidoyl radicals. Benzylic C−H bonds were selectively functionalized through photoredox catalysis starting from a sulfoximidoyl‐containing hypervalent iodine(III) reagent. The process is highly chemoselective and allows the conversion of a broad range of substrates. Mechanistic studies suggest the intermediacy of a sulfoximidoyl radical. Conceptionally, this represents a new approach towards sulfoximines.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201801660