Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids

Koichi Mitsudo; Takuya Shiraga; Jun Ichi Mizukawa; Seiji Suga; Hideo Tanaka

doi:10.1039/c0cc02633f

Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids

Koichi Mitsudo, Takuya Shiraga, Jun Ichi Mizukawa, Seiji Suga, Hideo Tanaka

Research output: Contribution to journal › Article

30 Citations (Scopus)

Abstract

An electro-oxidative method for generating silver acetylides from acetylenes with a Ag anode was developed. The reaction could be integrated into a Pd-catalysed electrochemical Sonogashira-type reaction. In the presence of the catalytic amount of Pd(OAc)₂ and 4-BzO-TEMPO, electro-generated silver acetylides reacted immediately with arylboronic acids to afford the corresponding coupling adducts in high yields.

Original language	English
Pages (from-to)	9256-9258
Number of pages	3
Journal	Chemical Communications
Volume	46
Issue number	48
DOIs	https://doi.org/10.1039/c0cc02633f
Publication status	Published - Dec 28 2010

Fingerprint

Alkynes

Silver

Anodes

Acids

Acetylene

TEMPO

palladium(II) acetate

ASJC Scopus subject areas

Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Catalysis
Chemistry(all)

Cite this

Mitsudo, K., Shiraga, T., Mizukawa, J. I., Suga, S., & Tanaka, H. (2010). Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids. Chemical Communications, 46(48), 9256-9258. https://doi.org/10.1039/c0cc02633f

Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids. / Mitsudo, Koichi; Shiraga, Takuya; Mizukawa, Jun Ichi; Suga, Seiji; Tanaka, Hideo.

In: Chemical Communications, Vol. 46, No. 48, 28.12.2010, p. 9256-9258.

Research output: Contribution to journal › Article

Mitsudo, K, Shiraga, T, Mizukawa, JI, Suga, S & Tanaka, H 2010, 'Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids', Chemical Communications, vol. 46, no. 48, pp. 9256-9258. https://doi.org/10.1039/c0cc02633f

Mitsudo K, Shiraga T, Mizukawa JI, Suga S, Tanaka H. Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids. Chemical Communications. 2010 Dec 28;46(48):9256-9258. https://doi.org/10.1039/c0cc02633f

Mitsudo, Koichi ; Shiraga, Takuya ; Mizukawa, Jun Ichi ; Suga, Seiji ; Tanaka, Hideo. / Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids. In: Chemical Communications. 2010 ; Vol. 46, No. 48. pp. 9256-9258.

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10.1039/c0cc02633f