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Light-promoted metal-free cross dehydrogenative couplings on ethers mediated by NFSI: reactivity and mechanistic studies

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Abstract

Cross dehydrogenative couplings on ethers occur very effectively using N-fluorobis(phenyl)sulfonimide (NFSI) as oxidizing agent under UVA irradiation in the presence of 2 mol% benzophenone. The reaction was shown to proceed first by fast radical fluorination of the α-C–H bond of ethers, followed by HF elimination to yield the highly electrophilic oxocarbenium ion as a key intermediate.

Graphical abstract: Light-promoted metal-free cross dehydrogenative couplings on ethers mediated by NFSI: reactivity and mechanistic studies

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Publication details

The article was received on 27 Jul 2017, accepted on 07 Nov 2017 and first published on 10 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC05854C
Citation: Chem. Commun., 2017, Advance Article
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    Light-promoted metal-free cross dehydrogenative couplings on ethers mediated by NFSI: reactivity and mechanistic studies

    R. Beniazza, B. Abadie, L. Remisse, D. Jardel, D. Lastécouères and J. Vincent, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC05854C

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