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, Natsuyo Kamimoto, Hiroki Murakami, Hiroki Mandai, Atsushi Wakamiya, Yasujiro Murata, Seiji Suga

Research output: Contribution to journalArticle

25 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9562-9569
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number48
DOIs
Publication statusPublished - 2012

Fingerprint

Diynes
Electricity
electricity
Oxidative Coupling
Thiophenes
Alkynes
alkynes
thiophenes
Fluorescence
Derivatives
fluorescence

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Site-selective sequential coupling reactions controlled by "electrochemical Reaction Site Switching" : A straightforward approach to 1,4-bis(diaryl)buta-1,3-diynes. / Mitsudo, Koichi; Kamimoto, Natsuyo; Murakami, Hiroki; Mandai, Hiroki; Wakamiya, Atsushi; Murata, Yasujiro; Suga, Seiji.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 48, 2012, p. 9562-9569.

Research output: Contribution to journalArticle

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