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Electronic Supplementary Information from Fe(OTf)3-catalysed Friedel–Crafts reaction of benzenoid arenes with α, β-unsaturated carbonyl compounds: easy access to 1,1-diarylalkanes

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journal contribution
posted on 09.10.2017, 09:53 by Aditya Bhattacharya, Pushpendra Mani Shukla, Biswajit Maji
A simple and efficient method for the synthesis of 1,1-diaryl alkanes via the Friedel–Crafts-type alkylation reaction of electron-rich arenes with cinnamic acid ester derivatives or chalcones is reported. Iron triflate has been found to be the best catalyst for the Friedel–Crafts-type alkylation reaction with α,β-unsaturated carbonyl compounds. This reaction afforded β,β-diaryl carbonyl compounds in good yields (65–93%) and with excellent regioselectivities. Remarkably, this method is also compatible with a variety of indoles to afford 3-indolyl-aryl carbonyl compounds in excellent yields. Great efforts have been made to deduce a plausible reaction mechanism based on isotopic labelling experiments.