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

Beniazza, Redouane; Abadie, Baptiste; Remisse, Lionel; Jardel, Damien; Lastécouères, Dominique; Vincent, Jean-Marc

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

2017

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.

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