15963-05-0Relevant articles and documents
Ferrocenium hexafluorophosphate as an inexpensive, mild catalyst for the etherification of propargylic alcohols
Queensen, Matthew J.,Rabus, Jordan M.,Bauer, Eike B.
, p. 221 - 229 (2015/08/06)
Commercial ferrocenium hexafluorophosphate ([FeCp2]PF6) 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 CH2Cl2, 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]PF6 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.
Etherification reactions of propargylic alcohols catalyzed by a cationic ruthenium allenylidene complex
Alkhaleeli, Doaa F.,Baum, Kevin J.,Rabus, Jordan M.,Bauer, Eike B.
, p. 45 - 48 (2014/02/14)
The cationic ruthenium allenylidene complex RRuR ax-[Ru(indenyl)L(PPh3)CCCPh2] +PF6 catalyzes the etherification of secondary and tertiary propargylic alcohols in a formal nucleophilic substitution reaction utilizing primary and secondary alcohols as the nucleophiles. At a catalyst loading of only 1.1 mol%, the corresponding propargylic ether products were obtained in 9 to 73% isolated yields (18 h reaction time at 100 C); no further additives are required. The reaction exhibits an induction period; as shown by a control reaction, the high reaction temperature may chemically change the allenylidene complex to be employed as the catalyst but does not lead to catalyst deactivation.
The coordination chemistry and reactivity of amino-dithiaphospholanes with rhodium, iridium, and ruthenium
Costin, Stephen,Sedinkin, Sergey L.,Bauer, Eike B.
scheme or table, p. 922 - 925 (2009/05/27)
Novel amino-dithiaphospholane complexes of ruthenium, iridium, and rhodium were synthesized, and their properties were studied. Reaction of the new amino-dithiaphospholane (RS)2PNR2′ (R = binaphthyl, R′ = CH2Ph,
