Deconstructive fluorination of cyclic amines by carbon-carbon cleavage

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Science  13 Jul 2018:
Vol. 361, Issue 6398, pp. 171-174
DOI: 10.1126/science.aat6365

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A silver cleaver splits cyclic amines

Carbon-carbon single bonds are fairly unreactive when they are not strained in a tight ring. Roque et al. now report that a silver salt can cleave C–C bonds in unstrained cyclic amines such as pyrrolidines and piperidines. Paired with an electrophilic fluorine source in aqueous solution, the silver first oxidizes the α carbon adjacent to the nitrogen. Ring-opening fluorination of the β carbon then proceeds by an apparent radical mechanism. The reaction offers a versatile means of introducing fluorine to structural motifs common in pharmaceutical research.

Science, this issue p. 171