Water-Promoted Suzuki Reaction in Room Temperature Ionic Liquids

Bingwei Xin; Yuhong Zhang; Leifang Liu; Yanguang Wang

doi:10.1055/s-2005-922756

LETTER

Water-Promoted Suzuki Reaction in Room Temperature Ionic Liquids

Bingwei Xin^a,b, Yuhong Zhang*^a, Leifang Liu^a, Yanguang Wang^a
^a Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87951512; e-Mail: yhzhang@zjuem.zju.edu.cn;
^b Department of Chemistry, Dezhou University, Dezhou 253023, P. R. of China

Abstract

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Abstract

The Suzuki reaction was successfully performed by using Pd(OAc)₂ as the catalyst in a mixture of water and ionic liquids in a short reaction time in air. Water was found to have a remarkable rate accelerating effect on the Suzuki reaction in ionic liquids. The Pd(OAc)₂-[bmim][PF₆] can be reused seven times only with a small deactivation of reactivity.

Key words

Suzuki reaction - ionic liquid - palladium acetate

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References

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General Procedure for Suzuki Reaction. To a mixture of [bmim][PF₆] and H₂O (3:1 g) {or [bmim][BF₄]-H₂O = 3:3 g} was added Na₂CO₃ (0.212 g,
2 mmol) and Pd (OAc)₂ (4 mg, 1.8 mol%).Then, the mixture was heated to 100 °C under stirring. Afterward, aryl halides (1 mmol) and arylboronic acid (1.5 mmol) was added in the solution and the reaction carried out at 100 °C for the indicated time. After the reaction, the reaction solution was cooled to r.t. and the resulting suspension was extracted with Et₂O (4 × 5 mL). In the recycle experiment, the residue after the extraction was washed with H₂O (3 × 6 mL) and then was subjected to a second run of the Suzuki reaction by charging with the same substrates (bromotoluene, phenylboronic acid, H₂O and Na₂CO₃) without further addition of Pd(OAc)₂ or ILs. The combined diethyl ether phase was analyzed by GC/MS and then concentrated. The further purification of the product was achieved by flash chromatography on a silica gel column. In the recycle experiments, the amount of the [bmim][PF₆]-H₂O was doubled.