Versatile Pd(OTf)2 x 2 H2O-catalyzed ortho-fluorination using NMP as a promoter.
Pd(OTf)(2) x 2 H(2)O-catalyzed ortho-fluorination of triflamide-protected benzylamines is reported. The use of N-fluoro-2,4,6-trimethylpyridinium triflate as the F(+) source and NMP as a promoter is crucial for this reaction. The conversion of triflamide into a wide range of synthetically useful functional groups makes this fluorination protocol broadly applicable in medicinal chemistry and synthesis.
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Xisheng
X
Wang
Tian-Sheng
TS
Mei
Jin-Quan
JQ
Yu
D001596:Benzylamines / Q000737:chemistry; D002384:Catalysis; D005464:Fluorobenzenes / Q000138:chemical synthesis*; D008698:Mesylates / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010879:Piperazines / Q000737:chemistry*; D014867:Water / Q000737:chemistry
C511391:1-(1-naphthylmethyl)piperazine; D001596:Benzylamines; D005464:Fluorobenzenes; D008698:Mesylates; D009942:Organometallic Compounds; D010879:Piperazines; D014867:Water; D010165:Palladium; C012077:trifluoromethanesulfonic acid