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.
Wang
Xisheng
X
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Mei
Tian-Sheng
TS
Yu
Jin-Quan
JQ
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