Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691-Stockholm, Sweden.
Department of Chemistry and Biotechnology, Tallinn University of Technology, 12618 Tallinn, Estonia.
Org Lett. 2023 Mar 24;25(11):1935-1940. doi: 10.1021/acs.orglett.3c00474. Epub 2023 Mar 10.
(Borylmethyl)trimethylsilanes are important building blocks in organic synthesis displaying a unique reactivity. Yet, the synthesis of more advanced derivatives is limited by the advanced silicon intermediates required for their preparation. Herein, a one-pot synthesis of (borylmethyl)silanes is developed, sourced on available alkyl-, aryl-, alkoxy-, aryloxy-, and silyl-hydrosilane materials. The privileged reactivity of -hydroxyphthalimidyl diazoacetate (NHPI-DA) in Si-H insertion and α-silyl redox-active esters in different decarboxylative borylation reactions are scrutinized.
（硼甲基）三甲基硅烷是有机合成中的重要结构单元，具有独特的反应性。然而，由于其制备所需的高级硅中间体，更高级别的衍生物的合成受到限制。本文开发了一种（硼甲基）硅烷的一锅合成方法，其原料为易得的烷基、芳基、烷氧基、芳氧基和硅基氢硅烷材料。考察了 -羟基邻苯二甲酰亚胺基重氮乙酸酯（NHPI-DA）在 Si-H 插入反应中的优势反应性，以及 α-硅基氧化还原活性酯在不同脱羧硼化反应中的反应性。
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