Metal-Free Direct Arylations of Indoles and Pyrroles with Diaryliodonium Salts

Direct arylations of indoles and pyrroles with differently substituted diaryliodonium salts were shown to efficiently proceed in the absence of metal catalysts.

DOI: 10.1021/ol200601e

Palladium-Catalyzed C–H Perfluoroalkylation of Arenes

A new Pd-catalyzed reaction for the coupling between perfluoroalkyl iodides (R_FI) and simple aromatic substrates is described. The perfluoroalkylated arene products are obtained in good to excellent yields in the presence of a phosphine-ligated Pd catalyst and Cs₂CO₃ as a base. The development, optimization, scope, and preliminary mechanistic studies of these transformations are reported.

http://pubs.acs.org/doi/abs/10.1021/ol200628n

PdCl2-catalyzed efficient allylation and benzylation of heteroarenes under ligand, base/acid, and additive-free conditions

Abstract

The Author present a PdCl₂-catalyzed protocol for highly efficient allylation and benzylation of a rich variety of N-, O-, and S-containing heteroarenes under base/acid, additive, and ligand-free conditions. The method represents the very few examples for simple, universally applicable, clean, and atom-efficient functionalization of heteroarenes.

DOI: 10.1039/C1CC10953G

Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl or Vinyl Chlorides to α-Ketoamides Through CCl Bond Activation

Nickeleophilic addition! The first example of a nickel-catalyzed direct intramolecular nucleophilic addition of aryl or vinyl chlorides to α-ketoamides through CCl bond activation is reported, which takes place under mild reaction conditions (see scheme).

DOI: 10.1002/chem.201100256

Regioselective Synthesis of Indenols by Rhodium-Catalyzed CH Activation and Carbocyclization of Aryl Ketones and Alkynes

Ketones and alkynes join together: The catalytic title reaction proceeds rapidly at 120 °C and requires only 1 hour for completion (see scheme). The reaction mechanism likely involves chelation-assisted ortho CH activation, insertion of the alkyne moiety, carbocyclization, and protonation. Cp*=pentamethylcyclopentadienyl.

DOI: 10.1002/anie.201100229

Base-Mediated Direct Arylation of Pyrrole Derivatives

Abstract

It appears that transition metal catalysts are not necessary to perform the direct arylation of electron-rich heterocycles with aryl iodides and bromides. Lithium tert-butoxide in DMF promotes this reaction for a variety of N-alkyl- and N-arylpyrroles as well as for benzofuran and some other electron-rich aromatic compounds and provides the desired products in moderate to high yields. In contrast to all previous reports on the Pd-catalyzed direct arylation of indolizine, the reaction mediated by lithium tert-butoxide proceeds selectively at position 5.

DOI: 10.1002/adsc.201000723

Mizoroki–Heck-Type Reaction Mediated by Potassium tert-Butoxide

In the absence of transition-metal catalysts, a Mizoroki–Heck-type reaction proceeded to give stilbene derivatives in a simple manner using an aryl halide, a styrene derivative, KOtBu, EtOH, and DMF (see scheme; DMF=N,N-dimethylformamide).

DOI: 10.1002/anie.201008220