Gold(I)-Catalyzed Synthesis of Highly Substituted Furans

Abstract

Cationic triphenylphosphinegold(I) complexes are excellent catalysts for a cascade reaction of propargyl-Claisen rearrangement and heterocyclization to synthesize tri- and tetrasubstituted furans. Starting from easily accessed propargyl vinyl ethers, the furans are obtained in 72-99% yield. [reaction: see text]

Silver‐Catalyzed One‐Pot Cyclization Reaction of Electron‐ Deficient Alkynes and 2‐Yn‐1‐ols: An Efficient Domino Process to Polysubstituted Furans

“…On the basis of these experimental results and previous reports, [14][15][16] a plausible reaction mechanism is shown in Scheme 4. The PBu 3 -promoted nucleoaddition of propargyl alcohol to electron-deficient alkynes formed enyne adduct A. Alkyne-coordinated silver B was generated from the intermediate A and Ag(I).…”

“…To the best of our knowledge, this transformation had not been reported in previous work. [14] The molecular structure of representative product 4fd was confirmed by an X-ray diffraction study ( Figure 1). …”

Metal-catalyzed Furan Synthesis. A Review

“…85,86 Jiang has recently published an Fe-catalyzed process which generally gives good yields of furans and requires a relatively inexpensive catalyst (Scheme 34). 87 The authors presented a one-pot process whereby DABCO, or tributylphosphine, catalyzed the addition of propargyl alcohols to activated alkynes and the resulting propargyl vinyl ethers were cyclized to the furan by the iron catalyst.…”

Gold(III)‐ und Platin(II)‐katalysierte Dominoreaktion aus Heterocyclisierung und 1,2‐Verschiebung: effiziente Synthese von hoch substituierten 3(2H)‐Furanonen

“…[4] In Weiterführung unserer Studien zu Kaskadenreaktionen, die durch übergangsmetallkatalysierte p-Aktivierung initiiert werden, [5] berichten wir hier über einen neuartigen Zugang zu 3(2H)-Furanonen durch eine katalysierte Kaskade aus Heterocyclisierung und 1,2-Verschiebung.…”