Attaching the fluorine atom to organic molecules using BrF3 and other reagents directly derived from F2

Research output: Contribution to journalArticlepeer-review

Abstract

Elemental fluorine is a starting point for nucleophilic fluorinations (e.g., BrF3), radical fluorinations (e.g., F2 under irradiation), and electrophilic fluorinations (e.g., AcOF). All three categories are represented in this Account. Bromine trifluoride, although commercially available, can be readily made from the elements and is a very good source for naked nucleophilic fluoride ions. To minimize radical reactions, an anchor has to be installed in the molecules with which it reacts. Such an anchor is constituted of a soft base such as nitrogen and especially sulfur atoms. This reagent was used for constructing compounds with a CF2, CF 3, CHF2, or CF2COOH group in specific sites. F2 itself was used for completing perfluorination of various polyfluoroethers, while the electrophilic acetyl hypofluorite is an excellent tool for introducing a single fluorine atom into organic molecules such as carboxylic acids and nitro compounds.

Original languageEnglish
Pages (from-to)803-812
Number of pages10
JournalAccounts of Chemical Research
Volume38
Issue number10
DOIs
StatePublished - Oct 2005

Fingerprint

Dive into the research topics of 'Attaching the fluorine atom to organic molecules using BrF3 and other reagents directly derived from F2'. Together they form a unique fingerprint.

Cite this