期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 18, 页码 5134-5138出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801280
关键词
C-H activation; charge transfer; fluorine; nitrogen heterocycles; regioselectivity
资金
- NSF
- MIT start-up funds
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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