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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-1H-indol-3-yl)acrylates.

A new one-pot approach was developed to construct the 11H-indolo[3,2-c]quinoline scaffold through a gold-catalysed reaction of 2-[(2-aminophenyl)ethynyl]phenylamine derivatives with aldehydes. The broad scope and the high regioselectivity of this new protocol as well as the mild and neutral reaction conditions make it a viable alternative to the previously reported procedures.

We present a method for the synthesis of substituted indolo[1,2‐a]quinoline‐5(6H)‐ones starting from 1‐(2‐ethynylphenyl)‐1H‐indoles. The transformation involves gold‐catalyzed oxidation of the triple bond followed by acid‐promoted intramolecular cyclization at the indole C2 position. Demonstrating noteworthy versatility, the reaction tolerates a wide array of substituents on the indole core and proceeds in good to excellent yields (up to 93 %). [ABSTRACT FROM AUTHOR]

The reactivity of vinyl‐/furoindole derivatives with gold‐activated π‐systems is the subject of extensive investigation. In the presence of these electrophilic partners, the realized transformations allow for the construction of different and fascinating architectures via cycloaddition and cyclization reactions often included in cascade processes. The reactions realized involving in these processes an external substituent at the indole moiety are the subject of the present minireview. [ABSTRACT FROM AUTHOR]

The gold-catalyzed synthesis of tetrahydrocarbazoles through dearomative [4+2] cycloaddition reactions of 3/2-substituted 2/3-vinylindoles with allenamides is reported. In particular, we optimized the enantioselective variant of these cycloadditions. Using allenamides as dienophiles 3-substituted 2-vinylindoles gave the corresponding carbazoles with high chemo-, regio- and enantioselectivity. Good results were obtained also with 2-methyl 3-vinylindoles even if mixtures of ( Z) and ( E) isomers were isolated in high er and in excellent overall yields. [ABSTRACT FROM AUTHOR]

A gold(I)-catalyzed cascade [3,3]-propargylic rearrangement and [4+2] cycloaddition reaction of 2-vinylindoles with propargylic esters is reported. The reaction leads to the synthesis of highly substituted tetrahydrocarbazole derivatives in high yields and diasteroselectivities. Furthermore, a preliminary screening for an asymmetric version of this reaction is described. [ABSTRACT FROM AUTHOR]

The review describes the most recently reported and efficient methods for the synthesis of heterocyclic compounds involving metal carbenes. In particular, copper, silver and gold carbenes, generated from suitable precursors, are involved in the synthesis of heterocyclic compounds through the formation of new carbon-heteroatom bonds. [Display omitted] [ABSTRACT FROM AUTHOR]

The gold-catalyzed intermolecular Diels-Alder cycloaddition and competitive Michael addition reactions between 2-vinylindoles and enones/enals are reported. The reaction outcome strictly correlates with the electronic character of the heteroaromatic substrate. Thus, Diels-Alder cycloadducts are the sole products in the presence of less electron-rich heterocycles, whereas Michael addition adducts are observed with more electron-rich heterocycles. Plausible competitive reaction mechanisms are proposed and discussed as well. [ABSTRACT FROM AUTHOR]

Abstract: In this account, we summarize the peculiar effects and advantages of gold, silver, and titanium dual role catalysis over the uncatalyzed tandem imination/annulation processes of γ- and δ-ketoalkynes. [ABSTRACT FROM AUTHOR]

Review: 124 refs. [ABSTRACT FROM AUTHOR]