1007605-49-3Relevant academic research and scientific papers
Gold- and silver-catalyzed reactions of propargylic alcohols in the presence of protic additives
Pennell, Matthew N.,Turner, Peter G.,Sheppard, Tom D.
, p. 4748 - 4758 (2012/05/04)
A wide range of primary, secondary and tertiary propargylic alcohols undergo a Meyer-Schuster rearrangement to give enones at room temperature in the presence of a gold(I) catalyst and small quantities of MeOH or 4-methoxyphenylboronic acid. The syntheses of the enone natural products isoegomaketone and daphenone were achieved using this reaction as the key step. The rearrangement of primary propargylic alcohols can readily be combined in a one-pot procedure with the addition of a nucleophile to the resulting terminal enone, to give β-aryl, β-alkoxy, β-amino or β-sulfido ketones. Propargylic alcohols bearing an adjacent electron-rich aryl group can also undergo silver-catalyzed substitution of the alcohol with oxygen, nitrogen and carbon nucleophiles. This latter reaction was initially observed with a batch of gold catalyst that was probably contaminated with small quantities of silver salt.
Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols
Georgy, Marie,Boucard, Valérie,Debleds, Olivier,Zotto, Christophe Dal,Campagne, Jean-Marc
experimental part, p. 1758 - 1766 (2009/06/28)
Gold-catalyzed nucleophilic substitution of propargylic alcohols with various nucleophiles (allylsilane, electron-rich aromatics, alcohols, thiols, hydrides, 1,3-dicarbonyl derivatives, sulfonamides) is described under very mild conditions (room temperatu
Zinc-mediated allylation of aryl 2-propynyl acetates: A facile synthesis of 1,5-enynes
Yadav,Subba Reddy,Chandrakanth,Prashant
scheme or table, p. 954 - 955 (2009/04/05)
Aryl 2-propynyl acetates undergo smooth allylation with allylzinc bromide (generated in situ from allyl bromide and zinc metal) in THF at room temperature under mild conditions to furnish the corresponding 1,5-enynes in good to excellent yields and with high selectivity. Indium metal is also found to accomplish the nucleophilic substitution of aryl 2-propynylic acetates with allyl bromide. Copyright
