Novel process for generating useful electrophiles from common anions using Selectfluor fluorination agent.
In the present work, the electrophile equivalents Cl+, Br+, SCN+, and NO2+ are generated from their respective sodium, potassium, and in some cases ammonium salts (M+X-) by reaction with Selectfluor electrophilic fluorination agent in acetonitrile solution at room temperature. These generated electrophilic species subsequently react in situ with a variety of aromatic substrates containing one or more substituent groups including H, F, Cl, CH3, COOH, C(O)CH3, NO2, and OR' and NR'R' ' where R' and R' ' are H or CH3. The resulting substitution products are, in most cases, isolable as pure compounds in high yield. Variations in the process include the use of other anions, electrophilic fluorination agents, and solvents.
Syvret
Robert G
RG
Fluorine Technology Center, Air Products and Chemicals, Inc., 7201 Hamilton Blvd., Allentown, Pennsylvania 18195, USA. syvretrg@apci.com
Butt
Kathleen M
KM
Nguyen
Tung P
TP
Bulleck
Victoria L
VL
Rieth
Ryan D
RD