Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid.
[reaction: see text] We have found new conditions for the Suzuki-Miyaura coupling reaction applicable to pentafluorophenylboronic acid (C(6)F(5)B(OH)(2)) (1), which is an inactive substrate under normal conditions. The reactions of 1 with phenyl iodide or bromide under Pd(PPh(3))(4)/CsF/Ag(2)O or Pd(2)(dba)(3)/P(t-Bu)(3)/CsF/Ag(2)O catalytic system conditions gave 2,3,4,5,6-pentafluoro-1,1'-biphenyl (3a) in more than 90% yields. Combination of CsF and Ag(2)O was essential for promoting these reactions.
Korenaga
Toshinobu
T
Department of Synthetic Chemistry, Graduate School of Natural Science and Technology, Okayama University, Japan. korenaga@cc.okayama-u.ac.jp
Kosaki
Takahiro
T
Fukumura
Rokki
R
Ema
Tadashi
T
Sakai
Takashi
T