Efficient Synthesis of 9,10-Bis(phenylethynyl)anthracene Derivatives by Integration of Sonogashira Coupling and Double-Elimination Reactions

Shinji Toyota; Daiki Mamiya; Rie Yoshida; Ryo Tanaka; Tetsuo Iwanaga; Akihiro Orita; Junzo Otera

doi:10.1055/s-0032-1316867

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(8): 1060-1068
DOI: 10.1055/s-0032-1316867

paper

Efficient Synthesis of 9,10-Bis(phenylethynyl)anthracene Derivatives by Integration of Sonogashira Coupling and Double-Elimination Reactions

Shinji Toyota*

^aDepartment of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan Fax: +81(86)2569457 eMail: stoyo@chem.ous.ac.jp

,

Daiki Mamiya

^aDepartment of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan Fax: +81(86)2569457 eMail: stoyo@chem.ous.ac.jp

,

Rie Yoshida

^aDepartment of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan Fax: +81(86)2569457 eMail: stoyo@chem.ous.ac.jp

,

Ryo Tanaka

^aDepartment of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan Fax: +81(86)2569457 eMail: stoyo@chem.ous.ac.jp

,

Tetsuo Iwanaga

^aDepartment of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan Fax: +81(86)2569457 eMail: stoyo@chem.ous.ac.jp

,

Akihiro Orita

^bDepartment of Applied Chemistry, Faculty of Engineering, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan

,

Junzo Otera

^bDepartment of Applied Chemistry, Faculty of Engineering, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan

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Abstract

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Abstract

9,10-Bis(phenylethynyl)anthracene (BPEA) derivatives were synthesized from 10-bromo-9-anthracenecarbaldehyde by stepwise Sonogashira coupling with phenylethynes and the one-shot double-elimination reaction with benzyl phenyl sulfones. Those two reactions could be integrated in a one-pot process to give unsymmetrically substituted BPEA derivatives in good yields by simple operations. This integrated process was applied to the synthesis of an extended BPEA derivative having an extra phenylethynyl group. The photophysical properties of the BPEA derivatives were investigated by UV/Vis and fluorescence spectroscopy.

Key words

alkynes - anthracenes - Sonogashira coupling - double elimination - one-pot process - reaction integration - fluorescence

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Referenzen

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