Fe(OTf)3-catalysed Friedel–Crafts reaction of benzenoid arenes with α, β-unsaturated carbonyl compounds: easy access to 1, 1-diarylalkanes. Issue 10 (25th October 2017)

• Record Type: Journal Article
• Authors: Bhattacharya, Aditya; Shukla, Pushpendra Mani; Maji, Biswajit
• Is Part Of: Royal Society open science. Volume 4:Issue 10(2017)
• Publication Date: 2017-10-25
• Subjects: Friedel–Crafts alkylation -- 1, 1-diarylalkane -- iron triflate -- β, β-diaryl carbonyl compounds; Science -- Periodicals; 500
• DOI: 10.1098/rsos.170748
• Languages: English
• ISSNs: 2054-5703

Abstract

Abstract : A simple and efficient method for the synthesis of 1, 1-diarylalkanes 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 provide 3-indolyl-aryl carbonyl compounds in excellent yields. Great efforts have been made to deduce a plausible reaction mechanism based on isotopic labelling experiments.