Benzylic Fluorination of Aza‐Heterocycles Induced by Single‐Electron Transfer to Selectfluor |
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| Authors: | Kelley E Danahy Julian C Cooper Prof?Dr Jeffrey F Van?Humbeck |
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| Institution: | 1. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, USA;2. Department of Chemistry, University of Calgary, Calgary, Alberta, Canada |
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| Abstract: | A selective and mild method for the benzylic fluorination of aromatic azaheterocycles with Selectfluor is described. These reactions take place by a previously unreported mechanism, in which electron transfer from the heterocyclic substrate to the electrophilic fluorinating agent Selectfluor eventually yields a benzylic radical, thus leading to the desired C?F bond formation. This mechanism enables high intra‐ and intermolecular selectivity for aza‐heterocycles over other benzylic components with similar C?H bond‐dissociation energies. |
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| Keywords: | C− H activation charge transfer fluorine nitrogen heterocycles regioselectivity |
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