Bhattacharya Aditya, Shukla Pushpendra Mani, Maji Biswajit
Department of Chemistry, Indira Gandhi National Tribal University, Amarkantak, Madhya Pradesh 484887, India.
R Soc Open Sci. 2017 Oct 25;4(10):170748. doi: 10.1098/rsos.170748. eCollection 2017 Oct.
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.
报道了一种通过富电子芳烃与肉桂酸酯衍生物或查耳酮的傅克型烷基化反应合成1,1-二芳基烷烃的简单有效方法。已发现三氟甲磺酸铁是与α,β-不饱和羰基化合物进行傅克型烷基化反应的最佳催化剂。该反应以良好的收率（65-93%）和优异的区域选择性得到β,β-二芳基羰基化合物。值得注意的是，该方法也与多种吲哚兼容，能以优异的收率提供3-吲哚基-芳基羰基化合物。基于同位素标记实验，人们已做出巨大努力来推导合理的反应机理。
