Di- and triheteroarylalkanes via self-condensation and intramolecular Friedel-Crafts type reaction of heteroaryl alcohols

Abstract

An efficient synthetic approach to diheteroarylmethanes and 1,3-diheteroarylpropenes has been developed via Yb(iii)-catalyzed sequential self-condensation of 2-furfuryl (or 2-thienyl or 3-indolyl) alcohols followed by intramolecular Friedel-Crafts type reaction and elimination of an aldehyde. This method offers a powerful entry and a potential alternative to the traditional synthesis of diheteroarylalkanes, which are precursors to the synthesis of several intriguing heteroaryls and more significantly, to the synthesis of biofuels. © 2013 The Royal Society of Chemistry.