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无溶剂高效合成氮杂环硅烷：温和条件下的有机催化方法

Solvent-Free and Efficient Synthesis of Silatranes an Organocatalytic Protocol under Mild Conditions.

作者信息

Oh Myong Joon, Kownacki Ireneusz, Kubicki Maciej

机构信息

Faculty of Chemistry, Adam Mickiewicz University in Poznan, Uniwersytetu Poznanskiego 8, 61-614 Poznan, Poland.

Center for Advanced Technology, Adam Mickiewicz University in Poznan, Uniwersytetu Poznanskiego 10, 61-614 Poznan, Poland.

出版信息

ACS Sustain Chem Eng. 2024 Jan 10;12(5):2049-2057. doi: 10.1021/acssuschemeng.3c07293. eCollection 2024 Feb 5.

DOI:10.1021/acssuschemeng.3c07293
PMID:38333205
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10848291/
Abstract

The organocatalytic approach to the formation of silatranyl cages permitted the design of a solvent-free and efficient protocol for the preparation of various organosilatranes. We discovered that amidine derivatives efficiently catalyze the conversion of trialkoxysilanes into organosilatranes, and their catalytic activity is related to the p values. NMR studies of equimolar reactions of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) with selected substrates allowed proposing a reliable scheme for the transesterification process and silatranyl cage formation. In addition, green chemistry metrics for the scaled-up synthesis of vinylsilatrane () were appointed. Finally, a scheme for the industrial production of silatrane derivatives with DBU and solvent regeneration was proposed, supported by a catalyst recycling experiment.

摘要

用于形成硅氮杂环笼的有机催化方法使得设计出一种无溶剂且高效的制备各种有机硅氮烷的方案成为可能。我们发现脒衍生物能有效地催化三烷氧基硅烷转化为有机硅氮烷，并且它们的催化活性与p值有关。对1,8 - 二氮杂双环[5.4.0]十一碳 - 7 - 烯（DBU）和1,5,7 - 三氮杂双环[4.4.0]癸 - 5 - 烯（TBD）与选定底物的等摩尔反应进行核磁共振研究，有助于提出一个关于酯交换过程和硅氮杂环笼形成的可靠方案。此外，还确定了乙烯基硅氮烷（）放大合成的绿色化学指标。最后，在催化剂循环利用实验的支持下，提出了一种利用DBU和溶剂再生进行硅氮烷衍生物工业化生产的方案。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/10848291/ee913ca5ff64/sc3c07293_0010.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/10848291/9e15e3a9d90a/sc3c07293_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/10848291/9edf505faeb6/sc3c07293_0006.jpg
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本文引用的文献

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