Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups. Effective application of the modified Suzuki-Miyaura coupling reaction

Toshinobu Korenaga, Takahiro Kosaki, Yusuke Kawauchi, Tadashi Ema, Takashi Sakai

Research output: Contribution to journal › Article

15 Citations (Scopus)

Abstract

A molecular tweezer bearing two pentafluorophenyl groups 2b and its o-methylated aryl homologue 2c were newly synthesized by the slight modification of the known procedure. The low yield in the introduction of pentafluorophenyl group to the precursor dibromide 6 was improved by application of the modified Suzuki-Miyaura coupling reaction using C6F5B(OH)2 with Pd2(dba)3/P(t-Bu)3/CsF/Ag2O catalytic system, which was recently developed by us.

Original languageEnglish
Pages (from-to)604-609
Number of pages6
JournalJournal of Fluorine Chemistry
Volume127
Issue number4-5 SPEC. ISS.
DOIs
Publication statusPublished - May 2006

Fingerprint

Bearings (structural)
dibromides
synthesis

Keywords

  • Molecular tweezer
  • Pentafluorophenyl group
  • Stacking interaction
  • Suzuki-Miyaura coupling

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics

Cite this

Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups. Effective application of the modified Suzuki-Miyaura coupling reaction. / Korenaga, Toshinobu; Kosaki, Takahiro; Kawauchi, Yusuke; Ema, Tadashi; Sakai, Takashi.

In: Journal of Fluorine Chemistry, Vol. 127, No. 4-5 SPEC. ISS., 05.2006, p. 604-609.

Research output: Contribution to journal › Article

Korenaga, T, Kosaki, T, Kawauchi, Y, Ema, T & Sakai, T 2006, 'Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups. Effective application of the modified Suzuki-Miyaura coupling reaction', Journal of Fluorine Chemistry, vol. 127, no. 4-5 SPEC. ISS., pp. 604-609. https://doi.org/10.1016/j.jfluchem.2005.12.007
Korenaga T, Kosaki T, Kawauchi Y, Ema T, Sakai T. Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups. Effective application of the modified Suzuki-Miyaura coupling reaction. Journal of Fluorine Chemistry. 2006 May;127(4-5 SPEC. ISS.):604-609. https://doi.org/10.1016/j.jfluchem.2005.12.007
Korenaga, Toshinobu ; Kosaki, Takahiro ; Kawauchi, Yusuke ; Ema, Tadashi ; Sakai, Takashi. / Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups. Effective application of the modified Suzuki-Miyaura coupling reaction. In: Journal of Fluorine Chemistry. 2006 ; Vol. 127, No. 4-5 SPEC. ISS. pp. 604-609.
@article{fa3ad96f0669467dab6bc2c766b5f220,
title = "Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups. Effective application of the modified Suzuki-Miyaura coupling reaction",
abstract = "A molecular tweezer bearing two pentafluorophenyl groups 2b and its o-methylated aryl homologue 2c were newly synthesized by the slight modification of the known procedure. The low yield in the introduction of pentafluorophenyl group to the precursor dibromide 6 was improved by application of the modified Suzuki-Miyaura coupling reaction using C6F5B(OH)2 with Pd2(dba)3/P(t-Bu)3/CsF/Ag2O catalytic system, which was recently developed by us.",
keywords = "Molecular tweezer, Pentafluorophenyl group, Stacking interaction, Suzuki-Miyaura coupling",
author = "Toshinobu Korenaga and Takahiro Kosaki and Yusuke Kawauchi and Tadashi Ema and Takashi Sakai",
year = "2006",
month = "5",
doi = "10.1016/j.jfluchem.2005.12.007",
language = "English",
volume = "127",
pages = "604--609",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier BV",
number = "4-5 SPEC. ISS.",

}

TY - JOUR

T1 - Synthesis of molecular tweezers bearing pentafluorophenyl and several pendant aryl groups. Effective application of the modified Suzuki-Miyaura coupling reaction

AU - Korenaga, Toshinobu

AU - Kosaki, Takahiro

AU - Kawauchi, Yusuke

AU - Ema, Tadashi

AU - Sakai, Takashi

PY - 2006/5

Y1 - 2006/5

N2 - A molecular tweezer bearing two pentafluorophenyl groups 2b and its o-methylated aryl homologue 2c were newly synthesized by the slight modification of the known procedure. The low yield in the introduction of pentafluorophenyl group to the precursor dibromide 6 was improved by application of the modified Suzuki-Miyaura coupling reaction using C6F5B(OH)2 with Pd2(dba)3/P(t-Bu)3/CsF/Ag2O catalytic system, which was recently developed by us.

AB - A molecular tweezer bearing two pentafluorophenyl groups 2b and its o-methylated aryl homologue 2c were newly synthesized by the slight modification of the known procedure. The low yield in the introduction of pentafluorophenyl group to the precursor dibromide 6 was improved by application of the modified Suzuki-Miyaura coupling reaction using C6F5B(OH)2 with Pd2(dba)3/P(t-Bu)3/CsF/Ag2O catalytic system, which was recently developed by us.

KW - Molecular tweezer

KW - Pentafluorophenyl group

KW - Stacking interaction

KW - Suzuki-Miyaura coupling

UR - http://www.scopus.com/inward/record.url?scp=33646398617&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33646398617&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2005.12.007

DO - 10.1016/j.jfluchem.2005.12.007

M3 - Article

VL - 127

SP - 604

EP - 609

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

IS - 4-5 SPEC. ISS.

ER -

Access to Document