Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid

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

doi:10.1021/ol051866i

Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid

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

Research output: Contribution to journal › Article › peer-review

103 Citations (Scopus)

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 language	English
Pages (from-to)	4915-4917
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	22
DOIs	https://doi.org/10.1021/ol051866i
Publication status	Published - Oct 27 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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T1 - Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid

AU - Korenaga, Toshinobu

AU - Kosaki, Takahiro

AU - Fukumura, Rokki

AU - Ema, Tadashi

AU - Sakai, Takashi

PY - 2005/10/27

Y1 - 2005/10/27

N2 - (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.

AB - (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.

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Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid

Abstract

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