2005/10/01 by Toshinobu Korenaga, Takahiro Kosaki, Rokki Fukumura +2 · 1 citation
Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Catalytic Cross-Coupling Reactions #Fluorine in Organic Chemistry #Organoboron and organosilicon chemistry
paper · doi:10.1021/ol051866i
openalex publication_date 2005/10/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26
[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.