Matthew J. Queensen, J. Rabus, Eike B. Bauer
Oct 1, 2015
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0
Influential Citations
9
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Journal
Journal of Molecular Catalysis A-chemical
Abstract
Abstract Commercial ferrocenium hexafluorophosphate ([FeCp 2 ]PF 6 ) was found to be an efficient catalyst for the etherification of terminal, tertiary propargylic alcohols with primary and secondary alcohols (5 h to 3 days reaction time at 40 °C in CH 2 Cl 2 , 3 mol% catalyst loading). The propargylic ether products were isolated in 90–20% yields. The alcohols and propargylic alcohols were employed in an equimolar amount and no further additives were required. For a purely aromatic propargylic alcohol, the isolated yields were lower than those for a mixed aromatic-aliphatic propargylic alcohol. Through monitoring reactant consumption and product formation over time, we found that the aromatic propargylic alcohol undergoes yield-diminishing Meyer–Schuster rearrangements to the aldehyde more easily than the mixed aromatic-aliphatic propargylic alcohol. The employment of [Fe(Cp) 2 ]PF 6 as a single electron oxidant has the potential to add a new direction in the development of catalysts for the title reaction based on single electron transfer processes.