Issue 48, 2012
From the journal:

Organic & Biomolecular Chemistry

Site-selective sequential coupling reactions controlled by “Electrochemical Reaction Site Switching”: a straightforward approach to 1,4-bis(diaryl)buta-1,3-diynes†

Koichi Mitsudo,*a   Natsuyo Kamimoto,a   Hiroki Murakami,a   Hiroki Mandai,a   Atsushi Wakamiya,b   Yasujiro Muratab  and  Seiji Suga*a  

* Corresponding authors

a Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsuhsima-naka, Kita-ku, Okayama 700-8530, Japan
E-mail: mitsudo@cc.okayama-u.ac.jp, suga@cc.okayama-u.ac.jp
Fax: +81 86 251 8081
Tel: +81 86 251 8081

b Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
E-mail: wakamiya@scl.kyoto-u.ac.jp, yasujiro@scl.kyoto-u.ac.jp
Fax: +81 774 38 3178
Tel: +81 774 38 3172

Abstract

Site-selective sequential coupling reactions directed toward bis(diaryl)butadiynes are described. The reaction site could be controlled completely by the on/off application of electricity. The electro-oxidative homo-coupling of terminal alkynes (electricity ON) and the subsequent Suzuki–Miyaura coupling (electricity OFF) afforded bis(diaryl)butadiynes in high yields. The obtained 1,4-bis(diaryl)butadiynes could be converted to a 2,5-bis(diaryl)thiophene derivative, which exhibited blue fluorescence.

Graphical abstract: Site-selective sequential coupling reactions controlled by “Electrochemical Reaction Site Switching”: a straightforward approach to 1,4-bis(diaryl)buta-1,3-diynes

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Article information

DOI
https://doi.org/10.1039/C2OB26567B
Article type
Paper
Submitted
08 Aug 2012
Accepted
22 Oct 2012
First published
23 Oct 2012

Org. Biomol. Chem., 2012,10, 9562-9569

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Site-selective sequential coupling reactions controlled by “Electrochemical Reaction Site Switching”: a straightforward approach to 1,4-bis(diaryl)buta-1,3-diynes

K. Mitsudo, N. Kamimoto, H. Murakami, H. Mandai, A. Wakamiya, Y. Murata and S. Suga, Org. Biomol. Chem., 2012, 10, 9562 DOI: 10.1039/C2OB26567B

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