One-Pot Cross-Coupling of Diborylmethane for the Synthesis of Dithienyl­methane Derivatives

Kohei Endo; Takafumi Ishioka; Takanori Shibata

doi:10.1055/s-0034-1378561

Synlett, Table of Contents

Synlett 2014; 25(15): 2184-2188
DOI: 10.1055/s-0034-1378561

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One-Pot Cross-Coupling of Diborylmethane for the Synthesis of Dithienylmethane Derivatives

Kohei Endo*

^aDivision of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan Fax: +81(76)2645698 Email: kendo@se.kanazawa-u.ac.jp Email: tshibata@waseda.jp

^bPRESTO, Japan Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan

,

Takafumi Ishioka

^cDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan

,

Takanori Shibata*

^cDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan

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Abstract

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Abstract

The one-pot palladium-catalyzed Suzuki–Miyaura cross-coupling reaction of a diborylmethane with bromothiophene derivatives realized the synthesis of various dithienylmethane derivatives. Cyclopentadithiophenes, which are promising compounds in material science, can be obtained in good yields. The in situ generation of an unstable thienylmethylboronate is a key step for the present reaction.

Key words

boron - cross-coupling - heterocycles - organometallic reagents - palladium

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References

References

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Supplementary Material

Supporting Information

One-Pot Cross-Coupling of Diborylmethane for the Synthesis of Dithienyl­methane Derivatives

One-Pot Cross-Coupling of Diborylmethane for the Synthesis of Dithienylmethane Derivatives