Keywords: Iron / Palladium / Indole / Bis(indolyl)methane Indoles were prepared by annulation of the parent alkynylanilines with the use of a new FeCl 3 -PdCl 2 catalytic combination. High yields were obtained by using low loadings of the transition-metal complex (FeCl 3 -PdCl 2 : 2 and 1 mol-%, respectively). One-pot accesses to bis(indolyl)methanes and trisubstituted indoles through annulation/Friedel-

International audienceHydroamination reactions of vinylarenes with nonnucleophilic nitrogen derivatives (p-toluenesulfonamide, p-nitroaniline, p-nitrobenzamide, ...) catalyzed by FeCl3 are described. Interestingly, these reactions are catalyzed by an environmentally friendly and an inexpensive catalyst in the absence of any ligand or cocatalyst

No abstract

No abstract

The synthesis of nicotinamide adenine dinucleotide (NAD) analogues in which the ribose unit of the nicotinamide moiety is replaced by a hexitol, altritol, and cyclohexenyl sugar mimic is described.

The intramolecular hydroarylation of alkynes using a substoichiometric amount of FeCl 3 is described. When starting from tetrasubstituted substrates, products resulting from an unexpected toluene (or xylene) elimination are isolated in good yields.The transition-metal-catalyzed hydroarylation of alkynes has quite recently emerged as an efficient and atom-economic methodology for the construction of functionalized aromatic compounds and styrene derivatives. [1][2][3][4][5] These reactions might be considered as potential alternatives to the well known Mirozoki-Heck and cross-coupling reactions. Ruthenium-, rhodium-, platinum-, gallium-, palladium-, indium-, mercury-, scandium-and gold-catalyzed reactions have recently been described in inter-and intramolecular hydroarylation reactions. 1,2 However, the high cost and/or toxicity of such metals precludes their large-scale use. The development of this type of atom-economic reaction with nontoxic and affordable catalyst is thus highly desirable. As part of a program directed toward the development of iron-catalyzed reactions, 6,7 the FeCl 3 -catalyzed intramolecular hydroarylation of alkynes was attempted (Scheme 1). During the preparation of this manuscript, Lu reported the FeCl 3 -catalyzed intermolecular hydroarylation of alkynes. 8 Examples of intramolecular reactions were, however, restricted to the synthesis of coumarins starting from phenylpropiolates. 8 In this letter, we wish to present our preliminary results on the intramolecular hydroarylation of alkynes.In the context of the synthesis of polyaromatic compounds, the intramolecular hydroarylation of compound 1a was investigated (Scheme 2). Initial experiments at 80 °C led to a complex mixture of the expected compound 2a along with products 3a and 4a resulting from the formal reduction and oxidation of 2a (Scheme 2). Gratifyingly, when the same reaction was carried out at room temperature, the amount of byproducts could be greatly reduced, and compound 2a was isolated in 84% yield.Scope and limitations were next explored and Figure 1 contains the results of an aromatic survey for this reaction. The reaction with unsubstituted aromatics (compound 2b, Figure 1) was somewhat tricky: whereas no reaction ocScheme 1 Intramolecular hydroarylation of alkynes R 1 R 2

Amines Q 0120 Intermolecular FeCl3-Catalyzed Hydroamination of Styrenes. -Environmentally friendly and inexpensive FeCl 3 catalyses the hydroamination of styrene derivatives without additional ligands or cocatalysts. -(MICHAUX, J.; TERRASSON, V.; MARQUE, S.; WEHBE, J.; PRIM*, D.; CAMPAGNE, J.-M.; Eur. J. Org. Chem.

A short asymmetric synthesis of optically pure beta-substituted beta-hydroxy aspartates is described. The key step is an aldol reaction between a glycine enolate derived from an oxazinone intermediate used as chiral auxiliary and various alpha-keto esters. Excellent diastereomeric excesses are obtained.