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J Org Chem. 2014 Sep 19;79(18):8895-9. doi: 10.1021/jo501520e. Epub 2014 Aug 27.

Triethylborane-initiated radical chain fluorination: a synthetic method derived from mechanistic insight.

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  • 1Department of Chemistry, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.


We offer a mild, metal-free sp(3) C-H fluorination alternative using Selectfluor and a substoichiometric amount of triethylborane-an established radical initiator in the presence of O2. This radical-chain-based synthetic method is particularly noteworthy as an offspring of the insight gained from a mechanistic study of copper-promoted aliphatic fluorination, constructively turning O2 from an enemy to an ally. Furthermore, BEt3/O2 is a preferred initiator in industrial processes, as it is economical, is low in toxicity, and lends way to easier workup.

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