Trimethylaluminum

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

“…Initially TMSOTf and BF 3 •OEt 2 were evaluated, as these Lewis acids are commonly employed with trichloroacetimidates. 16a,16c,16d With TMSOTf, however, the major product was the rearranged trichloroacetamide 8a , and this product was also a significant in the reaction with BF 3 •OEt 2 . This product has recently been observed to occur when trichloroacetimidate 6a is treated with a Lewis acid.…”

“…A survey of the literature suggested that trimethylaluminum may be a good candidate for this study as this reagent is readily available. Additionally, trimethylaluminum addition reactions are tolerant of and accelerated by exogenous Lewis acids, which are also known to facilitate trichloroacetimidate displacements. Trimethylaluminum has been used as a source of methyl anions previously to displace halides, sulfonates, , and Meldrum’s acid derivatives .…”