Solid-phase functionalization of heterocycles by direct lithiation

Abstract

Lithiation of polymer-bound 3-furanmethanol and 3-thiophenemethanol followed by the addition of electrophiles and resin cleavage afforded 2,4-disubsituted furans and thiophenes respectively in good yield. The 2,4-substituted thiophene can also be further lithiated on solid-phase at C-5 to give 2,3,5-substituted thiophenes.