Paper
Trifluoromethanesulfonic acid catalyzed friedel-Crafts alkylations of 1,2,4-trimethoxybenzene with aldehydes or benzylic alcohols.
Published May 3, 2013 · M. Wilsdorf, Daniel Leichnitz, H. Reissig
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Abstract
Trifluoromethanesulfonic acid in acetonitrile was found to efficiently catalyze Friedel-Crafts alkylations of 1,2,4-trimethoxybenzene with a variety of simple or functionalized aldehydes to provide di- or triarylmethanes in high yields. The operationally simple protocol allowed a short synthesis of the phenylpropanoid natural product (-)-tatarinoid C establishing its absolute configuration. Under the developed reaction conditions a benzylic alcohol instead of an aldehyde also underwent reactions with 1,2,4-trimethoxybenzene and other nucleophiles to afford unsymmetrically substituted compounds.
Trifluoromethanesulfonic acid in acetonitrile efficiently catalyzes Friedel-Crafts alkylations of 1,2,4-trimethoxybenzene with aldehydes or benzylic alcohols, enabling the synthesis of di- or
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