Beilstein J. Org. Chem.2020,16, 1436–1446, doi:10.3762/bjoc.16.119
University of Technology, Zeromskiego St. 116, 90-924 Lodz, Poland 10.3762/bjoc.16.119 Abstract The McKennareaction 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 McKennareaction 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 McKennareaction, 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
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Graphical Abstract
Scheme 1:
Schematic overview of the McKenna reaction including the decomposition of BTMS in protic solvents. ...