Journal
ORGANIC LETTERS
Volume 15, Issue 10, Pages 2494-2497Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol400972m
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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.
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