Justyna Katarzyna, Małolepsza Joanna, Kusy Damian, Maniukiewicz Waldemar, Błażewska Katarzyna M
Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego St. 116, 90-924 Lodz, Poland.
Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego St. 116, 90-924 Lodz, Poland.
Beilstein J Org Chem. 2020 Jun 23;16:1436-1446. doi: 10.3762/bjoc.16.119. eCollection 2020.
The McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into the target acids. However, the versatile character of the McKenna reaction is not always used to its full extent, due to formation of side products. Herein, demonstrated by using model examples we have not only analyzed the typical side processes accompanying the McKenna reaction, but also uncovered new ones. Further, we discovered that some commonly recommended precautions did not always circumvent the side reactions. The proposed results and recommendations may facilitate the synthesis of phosphonic acids.
麦肯纳反应是一种高效温和地合成有机磷酸的著名且常用方法。溴代三甲基硅烷（BTMS）是该反应中的主要试剂，它将膦酸二烷基酯转化为双（三甲基硅基）酯，然后这些双（三甲基硅基）酯可轻松转化为目标酸。然而，由于副产物的形成，麦肯纳反应的多功能性并未总是得到充分利用。在此，通过使用模型示例表明，我们不仅分析了伴随麦肯纳反应的典型副反应过程，还发现了新的副反应过程。此外，我们发现一些通常推荐的预防措施并不总能避免副反应。所提出的结果和建议可能有助于膦酸的合成。
