1590417-63-2Relevant academic research and scientific papers
Iron-catalyzed friedel-crafts benzylation with benzyl TMS ethers at room temperature
Sawama, Yoshinari,Shishido, Yuko,Kawajiri, Takahiro,Goto, Ryota,Monguchi, Yasunari,Sajiki, Hironao
supporting information, p. 510 - 516 (2014/04/03)
Friedel-Crafts benzylations between unactivated arenes and benzyl alcohol derivatives are clean and straightforward processes to construct biologically useful di- and triarylmethanes. We have established an efficient iron-catalyzed Friedel-Crafts benzylation method at room temperature that uses benzyl TMS ethers as substrates, which are poorly reactive under common nucleophilic substitution conditions. The reaction seems to progress through iron-catalyzed self-condensation of the benzyl TMS ether to the corresponding dibenzylic ether. The use of excess arene relative to benzyl TMS ether produced mono-benzylated arene (diand tri-arylmethane products), whereas the use of excess benzyl TMS ether versus arene provided bis-benzylated arene (polyarylated products) in high yields and regioselectivities. In previous methods, the latter double Friedel-Crafts benzylations hardly proceed.
Solvent-free Br?nsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano,Rucci, Marta,Spano, Giulia,Venturello, Paolo
, p. 1818 - 1826 (2014/03/21)
A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Br?nsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity was shown to be in agreement with Mayr's nucleophilicity and electrophilicity scales.
