Organic Chemistry

Lighting the way to fluorine placement

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Science  03 Mar 2017:
Vol. 355, Issue 6328, pp. 921-922
DOI: 10.1126/science.355.6328.921-g

Fluorination is a powerful strategy to fine-tune molecular properties in pharmaceutical research, but it is often difficult to place the F atoms exactly where you want them. Pitts et al. report a photochemical reaction applied to polycyclic terpenoid frameworks that reliably fluorinates C–H bonds three or four carbons away from the oxygen in an enone group. The site selectivity in one case distinguished among 65 different aliphatic C–H bonds. The authors postulate a radical mechanism involving H-atom abstraction by the enone in a triplet excited state.

J. Am. Chem. Soc. 10.1021/jacs.7b00335 (2017).

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