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Reagent for the Formation of Alkenylboronic Acid Esters

 The Takai reaction using 2-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1) and aldehydes affords the corresponding alkenylboronic acid esters under mild conditions. The reaction proceeds under neutral conditions at room temperature to afford the corresponding E-alkenylboronic acid esters in high yield and stereoselectivity. Although the reaction requires an excess amount of chromium(II) chloride, this can be decreased to a catalytic amount by using manganese as a reducing agent. It has been reported that bi-functionalized polyenes, which are difficult to synthesize using other methods, can be produced under mild conditions and applied to the synthesis of natural products.2)
Reagent for the Formation of Alkenylboronic Acid Esters


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