Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)-H arylation.

Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)–H arylation† †Electronic supplementary information (ESI) available: Detailed experimental procedures, analytical data. CCDC 1000469, 1007212 and 1019879. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02070g Click here for additional data file. Click here for additional data file.

Mechanistic studies on the copper-catalyzed N-arylation of amides.

The copper-catalyzed N-arylation of amides, i.e., the Goldberg reaction, is an efficient method for the construction of products relevant to both industry and academic settings. Herein, we present mechanistic details concerning the catalytic and stoichiometric N-arylation of amides. In the context of the catalytic reaction, our findings reveal the importance of chelating diamine ligands in cont...

Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design.

A palladium-pivalic acid cocatalyst system has been developed that exhibits unprecedented reactivity in direct arylation. This reactivity is illustrated with the first examples of high yielding direct metalation-arylation reactions of a completely unactivated arene, benzene. Experimental and computational evidence indicates that the pivalate anion is a key component in the palladation/C-H bond ...

Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides.

We present a novel and highly efficient methodology that allows for the construction of C-P bonds via the palladium-catalyzed air-based oxidative coupling of various commercially available arylboronic acids with easily oxidized H-phosphine oxides leading to valuable aryl phosphine oxides, particularly triarylphosphine oxides, with the use of air as the green oxidant, broad substrate applicabili...

Oxidative Arylation

The addition of aryl groups to unactivated olefins represents a direct approach to C!C bond construction. Pd-catalyzed coupling of aryl halides with alkenes, the Heck reaction, offers a viable approach to arylation. However, terminal unactivated olefins often display low reactivity in Heck reactions and can yield mixtures of styrenes and allyl arenes owing to poor regiocontrol in the b-hydride ...