2021The Journal of Organic ChemistryRequires access

Visible Light-Driven and Singlet Oxygen-Mediated Photochemical Cross-Dehydrogenative C 3 –H Sulfenylation of 4-Hydroxycoumarins with Thiols Using Rose Bengal as a Photosensitizer

Goutam Brahmachari, Anindita Bhowmick, Indrajit Karmakar

Open publisher page 60 citations

Abstract

A visible light (white light-emitting diode/direct sunlight)-driven photochemical synthesis of a new series of biologically interesting 3-(alkyl/benzylthio)-4-hydroxy-2 H -chromen-2-ones has been achieved through a cross-dehydrogenative C 3 –H sulfenylation of 4-hydroxycoumarins with thiols at ambient temperature in the presence of rose bengal in acetonitrile under an oxygen atmosphere. The notable features of this newly developed method are mild reaction conditions, energy efficiency, metal-free synthesis, good to excellent yields, use of low-cost materials, and eco-friendliness.

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A visible light (white light-emitting diode/direct sunlight)-driven photochemical synthesis of a new series of biologically interesting 3-(alkyl/benzylthio)-4-hydroxy-2 H -chromen-2-ones has been achieved through a cross-dehydrogenative C 3 –H sulfenylation of 4-hydroxycoumarins with thiols at ambient temperature in the presence of rose bengal in acetonitrile under an oxygen atmosphere. The notable features of this newly developed method are mild reaction conditions, energy efficiency, metal-free synthesis, good to excellent yields, use of low-cost materials, and eco-friendliness.

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Available abstract

A visible light (white light-emitting diode/direct sunlight)-driven photochemical synthesis of a new series of biologically interesting 3-(alkyl/benzylthio)-4-hydroxy-2 H -chromen-2-ones has been achieved through a cross-dehydrogenative C 3 –H sulfenylation of 4-hydroxycoumarins with thiols at ambient temperature in the presence of rose bengal in acetonitrile under an oxygen atmosphere. The notable features of this newly developed method are mild reaction conditions, energy efficiency, metal-free synthesis, good to excellent yields, use of low-cost materials, and eco-friendliness.

Key concepts: Rose bengal, Photosensitizer, Singlet oxygen, Photochemistry, Singlet state, Chemistry, BENGAL, Oxygen

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Visible Light-Driven and Singlet Oxygen-Mediated Photochemical Cross-Dehydrogenative C 3 –H Sulfenylation of 4-Hydroxycoumarins with Thiols Using Rose Bengal as a Photosensitizer — Research Paper | ScholarLens