An efficient method for regio- and chemoselective Friedel-Crafts acylation of indole using acyl chlorides in the presence of ZrCl(4) has been discovered. It minimizes/eliminates common competing reactions that occur due to high and multiatom-nucleophilic character of indole. In this method, a wide range of aroyl, heteroaroyl alkenoyl, and alkanoyl chlorides undergo smooth acylation with various indoles without NH protection and afford 3-acylindoles in good to high yields.
ZrCl 4 -Mediated Regio-and Chemoselective Friedel-Crafts Acylation of Indole. -It is found that ZrCl4 efficiently promotes regio-and chemoselective acylation of indoles yielding a wide range of 3-acylindoles. -(GUCHHAIT*, S. K.; KASHYAP, M.; KAMBLE, H.; J. Org. Chem. 76 (2011) 11, 4753-4758, http://dx.
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