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Synthesis of Siloxane Derivatives of Phenylboronic Acids of Different Structures
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2023-06-01 , DOI: 10.1021/acs.joc.3c00504
Elizaveta A Manokhina 1, 2 , Anton A Anisimov 1, 2, 3 , Fedor V Drozdov 1, 2, 4 , Rinat S Tukhvatshin 4 , Alexander S Peregudov 1 , Svetlana A Aksenova 1, 3 , Aziz M Muzafarov 1, 4
Affiliation  

The synthesis of a storage-stable organosilicon modifier with a dioxaborolane-protecting group is described. Its high reactivity and selective anti-Markovnikov addition in hydrosilylation reactions to afford siloxanes of various structures are shown. The possibility of deprotection of both the initial modifier and its siloxane derivatives under mild conditions using water in yields up to 96% is demonstrated. The existence of an equilibrium between the organosilicon derivatives of phenylboronic acids and their cyclic six-membered boroxines was confirmed by 1H NMR spectroscopy and X-ray diffraction analysis data. The use of siloxane derivatives of phenylboronic acids in Suzuki–Miyaura and Chan–Lam cross-coupling reactions was studied. All synthesized compounds were characterized by NMR (1H, 11B, 13C, and 29Si), IR spectroscopy, and high-resolution mass spectrometry.

中文翻译:

不同结构苯基硼酸硅氧烷衍生物的合成

描述了具有二氧硼杂硼烷保护基团的储存稳定的有机硅改性剂的合成。它在氢化硅烷化反应中表现出高反应性和选择性的抗马尔可夫尼科夫加成,以提供各种结构的硅氧烷。证明了在温和条件下使用水对初始改性剂及其硅氧烷衍生物进行脱保护的可能性,产率高达 96%。1 H NMR光谱和X射线衍射分析数据证实了苯基硼酸的有机硅衍生物与其环状六元环硼氧烷之间存在平衡。研究了苯基硼酸硅氧烷衍生物在 Suzuki-Miyaura 和 Chan-Lam 交叉偶联反应中的应用。所有合成的化合物均通过 NMR 进行表征(1H、11 B、13 C 和29 Si)、红外光谱和高分辨率质谱。
更新日期:2023-06-01
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