56138-25-1Relevant articles and documents
One-pot synthesis of 2-methylfurans from 3-(trimethylsilyl)propargyl acetates promoted by trimethylsilyl trifluoromethanesulfonate
Sklar, Danielle E.,Helbling, Alex V.,Liu, Yiqi,Downey, C. Wade
, (2021/11/01)
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine, 3-(trimethylsilyl)propargyl carboxylates undergo a one-pot alkylation-cyclization-desilylation reaction with ketones to produce 2-methylfurans. Alkylation at 0 °C in methylene chloride, followed by acid-catalyzed cyclization at room temperature, provides the furans in 52–86% yield. Cyclization and desilylation appear to be promoted by triflic acid generated in situ from the exposure of the reaction mixture to water upon completion of the initial substitution reaction.
Gold Catalyzed Synthesis of Substituted Furan by Intermolecular Cascade Reaction of Propargyl Alcohol and Alkyne
Hosseyni, Seyedmorteza,Su, Yijin,Shi, Xiaodong
supporting information, p. 6010 - 6013 (2016/01/09)
Using a combination of triazole-gold (TA-Au) and copper catalysts, the substituted furan was achieved in one pot through a three-step reaction cascade. The reaction tolerates a large substrate scope with simple starting materials. The desired di-, tri-, and tetrasubstituted furans were prepared in good to excellent yields.
Rhodium(III)-catalyzed alkenyl C-H bond functionalization: Convergent synthesis of furans and pyrroles
Lian, Yajing,Huber, Tatjana,Hesp, Kevin D.,Bergman, Robert G.,Ellman, Jonathan A.
supporting information, p. 629 - 633 (2013/02/23)
Ring in the new: A new annulation for the efficient synthesis of substituted furans and pyrroles is reported. The RhIII-catalyzed reaction of O-methyl α,β-unsaturated oximes with aldehydes and N-tosyl imines affords secondary alcohol and amine intermediates, respectively. Cyclization and aromatization occurs under the reaction conditions to provide access to biologically relevant furans and pyrroles in good yields. Cp=C5Me5, DCE=1,2-dichloroethane, THF=tetrahydrofuran. Copyright
