[Copper(I)(Pyridine-Containing Ligand)] Catalyzed Regio- and Steroselective Synthesis of 2‑Vinylcyclopropa[<i>b</i>]indolines from 2‑Vinylindoles

A [copper­(I)­pyridine-containing ligand]-catalyzed reaction between 2-vinylindoles and diazo esters is described. The reaction allows for the synthesis of a series of 2-vinylcyclopropa­[<i>b</i>]­indolines with excellent levels of regio- and sterocontrol under mild conditions

[Copper(I)(Pyridine-Containing Ligand)] Catalyzed Regio- and Steroselective Synthesis of 2‑Vinylcyclopropa[<i>b</i>]indolines from 2‑Vinylindoles

A [copper­(I)­pyridine-containing ligand]-catalyzed reaction between 2-vinylindoles and diazo esters is described. The reaction allows for the synthesis of a series of 2-vinylcyclopropa­[<i>b</i>]­indolines with excellent levels of regio- and sterocontrol under mild conditions

Gold-Catalyzed <i>cis</i>-Hydroarylation of Ynamides with Indoles: Regio- and Stereoselective Synthesis of a Class of 2‑Vinylindoles

A new gold-catalyzed reaction of ynamides with 3-substituted indoles as nucleophiles is reported. The reaction allows for the synthesis of a new class of 2-vinylindole derivatives in good yields via the intermediacy of a cyclopropyl gold-carbenoid species

Gold(I) or Silver Catalyzed Synthesis of α‑Indolylacrylates

Methyl 2-acetamidoacrylate reacted with various 2-substituted indoles in the presence of catalytic amounts of AgSbF₆ or AuPPh₃NTf₂ to provide the corresponding methyl 2-(2-substituted-1<i>H</i>-indol-3-yl)acrylates

Synthesis of Two Unnatural Oxygenated Aaptaminoids

Two unprecedented oxygenated aaptaminoids have been synthesized starting from cheap and easily available 2,3-dihydroxybenzoic acid with the satisfactory overall yields of 31% and 34%. The key step of the procedure is the divergent thermic 5-<i>exodig</i> vs base-promoted 6-<i>endodig</i> cyclization of a 5-alkynylquinolinone derivative

Synthesis of Two Unnatural Oxygenated Aaptaminoids

Two unprecedented oxygenated aaptaminoids have been synthesized starting from cheap and easily available 2,3-dihydroxybenzoic acid with the satisfactory overall yields of 31% and 34%. The key step of the procedure is the divergent thermic 5-<i>exodig</i> vs base-promoted 6-<i>endodig</i> cyclization of a 5-alkynylquinolinone derivative

Mild Regiospecific Synthesis of 1‑Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes

The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver­(I) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth ¹H NMR experiments and an aimed “trapping” experiment

[Silver(I)(Pyridine-Containing Ligand)] Complexes As Unusual Catalysts for A³‑Coupling Reactions

Two original macrocyclic silver­(I)­(pyridine-containing ligand) complexes [Ag­(I)­(Pc-L)] were synthesized and characterized. Their ability to catalyze the coupling among aldehydes, terminal alkynes and amines (A³-coupling) was demonstrated. The reaction could be performed under conventional as well as dielectric heating. The catalysts were effective in both cases, but dielectric heating allowed a lower catalyst loading and reduced ratio among reaction partners in shorter reaction times. The reaction scope was broad, including aryl/alkyl aldehydes, aryl/alkyl acetylenes and secondary aliphatic amines. Some unprecedented propargylamines have been prepared. The new catalytic system was also tested with more challenging coupling partners such as aniline and ketones