A Convenient Synthesis of Tetrasubstituted Furans from Propargylic Dithioacetals

Abstract

A convenient procedure for the regioselective synthesis of tetrasubstituted furans from the corresponding propargylic dithioacetals is described. Treatment of propargylic dithioacetals with n-BuLi and an aldehyde followed by mercuric acetate promoted annulation and desulfurization affords the corresponding mercurio-substituted furans. Subsequent replacement of the mercury moiety with iodine yields the corresponding 2,4,5-trisubstituted 3-iodofurans. Transition-metal-catalyzed cross-coupling reactions of the iodofurans furnish a variety of tetrasubstituted furans.

Key words

annulation - tetrasubstituted furan - propargylic dithioacetal - mercuric acetate - transition-metal-catalyzed cross-coupling

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