Oxidative cross-coupling of allyl(trimethyl)silanes with aryl boronic acids by palladium catalysis |
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Authors: | Zhibing Zhou Zhen-Lin Hou Fan Yang Bo Yao |
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Institution: | MOE Key Laboratory of Cluster Science, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 102488, PR China |
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Abstract: | The first oxidative cross-coupling of allylsilanes with aryl boronic acids has been developed by palladium catalysis. The reaction between β-substituted allyl(trimethyl)silanes and a wide range of aryl boronic acids afforded allylarenes in moderate to good yields and excellent selectivity. On the basis of experimental results and literature reports, it was suggested that the reaction might start from transmetalation of aryl boronic acid with AgOAc followed by transmetalation with Pd(II) to give an arylpalladium acetate complex as a key intermediate. This intermediate underwent either electrophilic addition/desilylation or transmetalation with allylsilane and subsequent reductive elimination to give the final product. |
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Keywords: | Oxidative cross-coupling Palladium catalysis Allyl(trimethyl)silane Aryl boronic acid |
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