Facile hydroboration of (Z)-1-trimethylsilyl-1-alkenes with dichloroborane-dioxane complex: An easy access to gem-dimetalloalkanes containing boron and silicon |
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Authors: | Narayan G Bhat Mary A Villanueva |
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Institution: | Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541, USA |
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Abstract: | (Z)-1-trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes followed by protonolysis with acetic acid, readily react with dichloroborane-dioxane complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in dichloromethane at 0 °C for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These α-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing α-trimethylsilyl group in 78-88% isolated yields. |
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Keywords: | Hydroboration gem-Dimetalloalkanes Dichloroborane-dioxane complex 1-Trimethylsilylalkynes (Z)-1-trimethylsilyl-1-alkenes |
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