A Practical Protocol for the Hiyama Cross-Coupling Reaction Catalyzed by Palladium on Carbon

Yasunari Monguchi; Takayoshi Yanase; Shigeki Mori; Hironao Sajiki

doi:10.1055/s-0032-1316801

Synthesis, Table of Contents

Synthesis 2013; 45(1): 40-44
DOI: 10.1055/s-0032-1316801

practical synthetic procedures

A Practical Protocol for the Hiyama Cross-Coupling Reaction Catalyzed by Palladium on Carbon

Yasunari Monguchi*

Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan Fax: +81(58)2308109 Email: monguchi@gifu-pu.ac.jp Email: sajiki@gifu-pu.ac.jp

,

Takayoshi Yanase

Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan Fax: +81(58)2308109 Email: monguchi@gifu-pu.ac.jp Email: sajiki@gifu-pu.ac.jp

,

Shigeki Mori

Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan Fax: +81(58)2308109 Email: monguchi@gifu-pu.ac.jp Email: sajiki@gifu-pu.ac.jp

,

Hironao Sajiki*

Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan Fax: +81(58)2308109 Email: monguchi@gifu-pu.ac.jp Email: sajiki@gifu-pu.ac.jp

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Abstract

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Abstract

A method for the palladium on carbon (Pd/C) catalyzed cross-coupling reaction between aryl halides and trialkoxy(aryl)silanes in the presence of a small amount of water is established using tris(4-fluorophenyl)phosphine as the ligand. A range of biaryl compounds is prepared using this protocol.

Key words

palladium - cross-coupling - heterogeneous - silicon - biaryls

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References

References

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14 The palladium particle size and carbon surface area of the 10% Pd/C (K-type, N.E. Chemcat Corporation) used in this study are approximately 5 nm and 1100 m²/g, respectively.
15 The protocol and outcome of the cross-coupling between 1-iodo-4-nitrobenzene and triethoxy(phenyl)silane was not affected when 10% Pd/C obtained from different suppliers was used (see Table 6).
16 When Pd(OAc)₂ (5 mol%), as a homogeneous catalyst, and (4-FC₆H₄)₃P (20 mol%) were used for the cross-coupling of 1-iodo-4-nitrobenzene with triethoxy(phenyl)silane (1.5 equiv) in 4.8% aqueous toluene at 120 °C (bath temperature), the desired 4-nitrobiphenyl was obtained in 72% yield, together with the homo-coupled product derived from the iodide, 4,4′-dinitrobiphenyl, in 5% yield. The use of 10% Pd/C was more appropriate for the present conditions compared to those applied in Table 3, entry 7; see also the supporting information in our previous communication.¹¹

In the presence of a small amount of water, the alkoxy groups of the triethoxy(aryl)silane would be hydrated into the corresponding hydroxy groups, and the electrophilicity of the silicon atom would increase. On the other hand, addition of an excess amount of water resulted in the formation of inactive caged siloxane derivatives, see reference 11 and:

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Supplementary Material

Supporting Information