1379804-82-6Relevant academic research and scientific papers
HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols
Barreiro, Elena,Sanz-Vidal, Alvaro,Tan, Eric,Lau, Shing-Hing,Sheppard, Tom D.,Dez-Gonzlez, Silvia
, p. 7544 - 7549 (2016/01/26)
The activity of HBF4 (aqueous solution) as a catalyst in propargylation reactions is presented. Diverse types of nucleophiles were employed in order to form new C-O, C-N and C-C bonds in technical acetone and in air. Good to excellent yields and good chemoselectivities were obtained using low acid loading (typically 1 mol-%) under simple reaction conditions. The activity of HBF4 (aq. solution) as a catalyst in propargylation reactions is presented. C-O, C-N and C-C bonds were formed in technical acetone and in air. Good to excellent yields were obtained using low acid loading (typically 1 mol-%) under mild reaction conditions.
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.
