Attaching the fluorine atom to organic molecules using BrF3 and other reagents directly derived from F2.
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, CF3, 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.
Rozen
Shlomo
S
School of Chemistry, Tel-Aviv University, Tel-Aviv 69978, Israel. rozens@post.tau.ac.il
D001966:Bromine / Q000737:chemistry*; D017605:Bromine Compounds / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D017611:Fluorine Compounds / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D008956:Models, Chemical; D009930:Organic Chemicals / Q000737:chemistry*
D017605:Bromine Compounds; D017611:Fluorine Compounds; D007202:Indicators and Reagents; D009930:Organic Chemicals; D005461:Fluorine; C507211:bromine trifluoride; D001966:Bromine