volume 32 , issue 3 , pages 432-434

Regiospecific Conversion of 3,4-Bis(trimethylsilyl)furan to 3,4-Disubstituted Furans: A Novel Suzuki-Type Cross-Coupling of Boroxines†

Zhi-Zhong Song ¹

Zhong-Yuan Zhou ¹

Thomas C. W. Mak ¹

Henry N. C. Wong ¹

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Department of Chemistry The Chinese University of Hong Kong Shatin, New Territories, Hong Kong |

Publication type: Journal Article

Publication date: 1993-03-01

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DOI: 10.1002/anie.199304321

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General Chemistry

Catalysis

Abstract

A versatile building block is found in the easily accessible 3,4-bis(trimethylsilyl)furan, which can be converted into boroxine 1 with BCl3 followed by aqueous workup. Subsequent Pd-catalyzed treatment with organic halides furnishes monoorganosilylfuran. Repetition of this reaction sequence affords 3,4-disubstituted furans, which are difficult to obtain by other methods.

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