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Synthesis of 1,1'-Diarylethanes and Related Systems by Displacement of Trichloroacetimidates with Trimethylaluminum

Nivedita S. Mahajani and John D. Chisholm*

*Department of Chemistry, Syracuse University, 1-014 Center for Science and Technology, Syracuse, New York 13244, United States, Email:

N. S. Mahajani, J. D. Chisholm, J. Org. Chem., 2018, 83, 4131-4139.

DOI: 10.1021/acs.joc.8b00027

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The reaction of benzylic trichloroacetimidates with trimethylaluminum under Lewis acid promoted conditions provides the corresponding methylated products. Most benzylic trichloroacetimidates undergo ready displacement, with electron deficient systems being the exception. The use of an enantiopure imidate showed significant racemization, implicating the formation of a cationic intermediate.

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ID: J42-Y2018