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

doi:10.1016/j.jfluchem.2005.12.007

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 › peer-review

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 language	English
Pages (from-to)	604-609
Number of pages	6
Journal	Journal of Fluorine Chemistry
Volume	127
Issue number	4-5 SPEC. ISS.
DOIs	https://doi.org/10.1016/j.jfluchem.2005.12.007
Publication status	Published - May 2006

Keywords

Molecular tweezer
Pentafluorophenyl group
Stacking interaction
Suzuki-Miyaura coupling

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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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 › peer-review

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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",

note = "Funding Information: This work was partially supported by Okayama Foundation for Science and Technology, and a Grant-in-Aid for Young Scientists (B) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. We thank the SC-NMR Laboratory of Okayama University for 1 H, 13 C, and 19 F NMR measurements. We are grateful to Dr. Teruhiko Nitoda in Okayama University for his kind assistance in the measurement of mass spectra.",

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doi = "10.1016/j.jfluchem.2005.12.007",

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AU - Korenaga, Toshinobu

AU - Kosaki, Takahiro

AU - Kawauchi, Yusuke

AU - Ema, Tadashi

AU - Sakai, Takashi

N1 - Funding Information: This work was partially supported by Okayama Foundation for Science and Technology, and a Grant-in-Aid for Young Scientists (B) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. We thank the SC-NMR Laboratory of Okayama University for 1 H, 13 C, and 19 F NMR measurements. We are grateful to Dr. Teruhiko Nitoda in Okayama University for his kind assistance in the measurement of mass spectra.

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

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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