无金属条件下合成Gem-硅基硼酸酯及其与芳基碘化物的 Pd(0)催化交叉偶联反应。
Metal-free synthesis of gem-silylboronate esters and their Pd(0)-catalyzed cross-coupling with aryliodides.
机构信息
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
出版信息
Org Biomol Chem. 2019 Jun 12;17(23):5714-5724. doi: 10.1039/c9ob01006h.
A transition-metal-free method for the synthesis of gem-silylboronate esters with arylboronic acids and trimethylsilyldiazomethane (TMSCHN2) has been developed. This transformation is a straightforward homologation of arylboronic acids and features wide substrate scope and good functional-group tolerance. The gem-silylboronate esters undergo efficient Suzuki-Miyaura cross-coupling with aryliodides and the silyl group of the product can be further functionalized. Tertiary carbon centers with different substituents can be constructed successfully by selective and sequential functionalization.
发展了一种无过渡金属的方法，用于合成芳基硼酸和三甲基硅基重氮甲烷（TMSCHN2）的偕二硅基硼酸盐酯。这种转化是芳基硼酸的直接同系化反应，具有广泛的底物范围和良好的官能团容忍度。偕二硅基硼酸盐酯与芳基碘化物发生有效的 Suzuki-Miyaura 交叉偶联，产物中的硅基可以进一步官能化。通过选择性和顺序官能化，可以成功构建具有不同取代基的叔碳中心。
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