TY  - JOUR
A1  - Madani, Amiera
A1  - Anghileri, Lucia
A1  - Heydenreich, Matthias
A1  - Möller, Heiko Michael
A1  - Pieber, Bartholomäus
T1  - Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch
JF  - Organic letters / publ. by the American Chemical Society
N2  - We present a divergent strategy for the fluorination of phenylacetic acid derivatives that is induced by a charge-transfer complex between Selectfluor and 4-(dimethylamino)pyridine. A comprehensive investigation of the conditions revealed a critical role of the solvent on the reaction outcome. In the presence of water, decarboxylative fluorination through a single-electron oxidation is dominant. Non-aqueous conditions result in the clean formation of alpha-fluoro-alpha-arylcarboxylic acids.
KW  - Charge transfer
KW  - Halogenation
KW  - Oxidation
KW  - Reaction products
KW  - Reagents
Y1  - 2022
U6  - https://doi.org/10.1021/acs.orglett.2c02050
SN  - 1523-7060
SN  - 1523-7052
VL  - 24
IS  - 29
SP  - 5376
EP  - 5380
PB  - American Chemical Society
CY  - Washington
ER  -