Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid

Toshinobu Korenaga, Takahiro Kosaki, Rokki Fukumura, Tadashi Ema, Takashi Sakai

Research output: Contribution to journalArticle

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Abstract

(Chemical Equation Presented) We have found new conditions for the Suzuki-Miyaura coupling reaction applicable to pentafluorophenylboronic acid (C6F5B(OH)2) (1), which is an inactive substrate under normal conditions. The reactions of 1 with phenyl iodide or bromide under Pd(PPh3)4/CsF/Ag2O or Pd 2(dba)3/ P(t-Bu)3/CsF/Ag2O catalytic system conditions gave 2,3,4,5,6-pentafluoro-1,1′-biphenyl (3a) in more than 90% yields. Combination of CsF and Ag2O was essential for promoting these reactions.

Original languageEnglish
Pages (from-to)4915-4917
Number of pages3
JournalOrganic Letters
Volume7
Issue number22
DOIs
Publication statusPublished - Oct 27 2005

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Iodides
Bromides
acids
Acids
Substrates
iodides
bromides
diphenyl

ASJC Scopus subject areas

  • Molecular Medicine

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Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid. / Korenaga, Toshinobu; Kosaki, Takahiro; Fukumura, Rokki; Ema, Tadashi; Sakai, Takashi.

In: Organic Letters, Vol. 7, No. 22, 27.10.2005, p. 4915-4917.

Research output: Contribution to journalArticle

Korenaga, T, Kosaki, T, Fukumura, R, Ema, T & Sakai, T 2005, 'Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid', Organic Letters, vol. 7, no. 22, pp. 4915-4917. https://doi.org/10.1021/ol051866i
Korenaga, Toshinobu ; Kosaki, Takahiro ; Fukumura, Rokki ; Ema, Tadashi ; Sakai, Takashi. / Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid. In: Organic Letters. 2005 ; Vol. 7, No. 22. pp. 4915-4917.
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