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Silver-mediated phosphacyclic ring expansion with strategic placement of phosphorus and dimethyl acetylenedicarboxylate (DMAD) on Vat Orange 3 was carried out. The target compounds possess narrow HOMO...

Alkyne- and alkene-tethered acyl fluorides undergo intramolecular carbofluorination via fluoride recycling using catalytic TrBF4. Excellent stereoselectivity is observed for the alkyne addition, enabling access to novel fluorinated indan-2-ones (all ≥95:5 E/Z) and cyclopentan-2-ones (85:15 E/Z). Fluorinated chroman-2-ones and tertiary alkyl fluorides can also be synthesized using this method, comparing favorably to previously reported protocols that employ expensive metal catalysts under harsher conditions.