Nucleophilic Addition of 1,1′-Bis(hydroxymethyl)ferrocene to Alkynes: Synthesis of Ferrocene Diethenyl Ethers

Abstract

Chemoselective and atom-economical methods for the synthesis of ferrocene diethenyl ethers have been developed via direct base-catalyzed addition of 1,1′-bis(hydroxymethyl)ferrocene to various acetylenes. This ferrocene diol has been shown to be capable of adding to acetylene (KOH/DMSO, 70–80 °C, 1–3 h), propyne (KOH/DMSO, 70 °C, 12 h), phenylethyne (KOH/DMSO, 20–25 °C, 48 h), alkylpropiolates (DABCO, 10 mol%/CH₂Cl₂, 20–25 °C, 0.5 h), and acylacetylenes (DABCO, 1 mol%/CH₂Cl₂, 20–25 °C, 0.5 h) to afford the corresponding diethenyl ethers in 73–98% yields.

Key words

alkynes - 1,1′-bis(hydroxymethyl)ferrocene - nucleophilic addition - diethenyl ethers - regioselectivity

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