Aromatic Fluorinations Suitable for Fluorine-18 Labeling of Estrogens

Johny S. Ng, John A. Katzenellenbogen, Michael R. Kilbourn

Research output: Contribution to journalArticlepeer-review


Two aromatic fluorination methods, the decomposition of aryl azides and the decomposition of aryltriazenes, were investigated as methods potentially suitable for fluorine-18 labeling of estrogens. The aryltriazene method gives moderate yields in many systems but fails with o-methoxy or (methanesulfonyl) oxy groups. The aryl azide method gives good yields of p-fluoroanilines, which can be deaminated readily, but oxygen or large alkyl groups ortho to the azide interfere with the fluorination. The synthesis of m-fluorohexestrol via the aryltriazene decomposition approach is reported.

Original languageEnglish (US)
Pages (from-to)2520-2528
Number of pages9
JournalJournal of Organic Chemistry
Issue number12
StatePublished - Jun 1981

ASJC Scopus subject areas

  • Organic Chemistry


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