Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes

Abstract

Functionalized furans are conveniently formed by a new silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol. Evidence supported a cascade mechanism.

Silver‐Catalyzed Atom‐Economic Hydrophosphorylation of Propargyl Epoxides: An Access to 4‐Phosphoryl 2,3‐Allenols and Stereodefined 1‐Phosphoryl 1,3‐Dienes

“…However, it turns out that several bench available Au salts such as AuCl, Ph 3 PAuCl and a NHCAuCl(NHC = 1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene) are all less reactive (entries [14][15][16][17][18][19][20]. Using Ag 2 CO 3 as the catalyst, an examination on the solvent effect was then undertaken.…”

Ring Expansions of Oxiranes and Oxetanes

“…Professor Pale and his colleagues have reported that α-alkynyl-substituted oxiranes can be converted in one step to furan in the presence of a silver catalyst, AgOTf, and an organic acid (Scheme 22) [30]. The reaction proceeds at room temperature in a DCM-methanol solvent mixture (9:1).…”

Carbo- and heterocyclisation of oxygen- and nitrogen-containing electrophiles by platinum, gold, silver and copper species

“…Pale et al 25 and 1,3-diketones 28-3 depending on whether alcohol is present; a mechanism is proposed in Scheme 28. 26c In this complicated pathway, formation of difurylmethane species 28-2 is derived from the coupling of cations 28c and their alcohol derivatives.…”