BF3.OEt2-Mediated Benzylation of Arenes and Heteroarenes with Benzyl Ether Derivatives英文文献资料.docVIP

International Journal of Organic Chemistry, 2011, 1, 176-182 doi:10.4236/ijoc.2011.14026 Published Online December 2011 (http://www.SciRP.org/journal/ijoc) BF3·OEt2-Mediated Benzylation of Arenes and Heteroarenes with Benzyl Ether Derivatives Ling Dang, Qiang Li, Tongmei Ma , Sheng Sheng, Wei Zeng * * School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China E-mail: { zengwei, tongmei}@ Received October 18, 2011; revised November 26, 2011; accepted December 3, 2011 * * Abstract An efficient BF3·Et2O-promoted benzylation of arenes and heteroarenes with various benzyl ether derivatives has been developed. This method provided alternative access to valuable diarylmethane in good yields under mild conditions via an easy work-up procedure. Keywords: Friedel-Crafts Alkylation, BF3·Et2O, Diarylmethane, Benzyl Ether Derivatives, Arenes 1. Introduction ethers as alkyalting agents. During the period that we investigated the effect of various Lewis acids on the N- alkylation of 4-toluene sulfonamide 5 in toluene solvent, we found BF3·Et2O could enhance the formation of by- product diarylmethane 3a and 4a (around 10% yield) from the alkyaltion of toluene 2a and benzyl ether 1a (see Scheme 1), and further studies indicated that bypro- duct diarylmethane 3a and 4a did not form in the pres- ence of other Lewis acids including AlCl3, TiCl4, Cu- (OAc)2·2H2O, CdCl2·2.5H2O, ZrCl4, MgO, etc. Herein, we reported our further studies about BF3·Et2O-promoted benzylation of arenes with benzyl ether derivatives. Diarylmethane motifs are an important class of aromatic building blocks which are found in various biologically active compounds such as anastrozole, papaverine, piri- trexim, avrainvilleol, and beclobrate [1-5]. They are also used as key precursors in the synthesis of electroactive and photoactive oligomers