Abstract：
A method has been described for accessing α-seleno alkyl boronates. The selenoboration was achieved via the diboration of carbonyl compounds to give α-oxyl boronates, which then undergo 1,2-metalate rearrangement in the presence of lithium selenolates and trifluoroacetic anhydride (TFAA). A variety of structurally diverse substrates were compatible with this protocol and efficiently provides difunctionalized products from simple starting materials. The presence of the boronic ester in the resulting organoselenium compounds serves as a versatile synthetic handle for various functionalizations. Mechanistic studies revealed that the binding of selenium nucleophile to both the boron centers in α-oxyl boronate esters.
摘要：
已经描述了一种用于获得α-硒代烷基硼酸酯的方法。通过羰基化合物的二硼化反应获得α-氧基硼酸酯，然后在硒酸锂和三氟乙酸酐（TFAA）的存在下进行1,2-金属酸盐重排。多种结构上不同的底物与该方案相容,并且从简单的起始材料有效地提供双官能化产物。硼酸酯在所得有机硒化合物中的存在充当各种官能化的通用合成处理。机理研究表明，硒亲核试剂与α-氧基硼酸酯中的两个硼中心都结合。
