Palladium-Catalyzed Ring-Opening Reaction of Oxa/Azabenzonorbornadienes with Aryl Acetylenes

Copper(I)-Catalyzed Coupling of Terminal Acetylenes with Aryl or Vinyl Halides Copper(I)-Catalyzed Coupling of Terminal Acetylenes

Palladium-catalyzed ring-opening reactions of cyclopropanated 7-oxabenzonorbornadiene with alcohols

Palladium-catalyzed ring-opening reactions of cyclopropanated 7-oxabenzonorbornadiene derivatives using alcohol nucleophiles were investigated. The optimal conditions were found to be 10 mol % PdCl2(CH3CN)2 in methanol, offering yields up to 92%. The reaction was successful using primary, secondary and tertiary alcohol nucleophiles and was compatible with a variety of substituents on cyclopropa...

Palladium-catalyzed synthesis of N-aryl carbamates.

An efficient synthesis of aryl carbamates was achieved by introducing alcohols into the reaction of palladium-catalyzed cross-coupling of ArX (X = Cl, OTf) with sodium cyanate. The use of aryl triflates as electrophilic components in this transformation allowed for an expanded substrate scope for direct synthesis of aryl isocyanates. This methodology provides direct access to major carbamate pr...

Palladium-Catalyzed α-Arylation of Aryl Nitromethanes

Catalytic conditions for the α-arylation of aryl nitromethanes have been discovered using parallel microscale experimentation, despite two prior reports of the lack of reactivity of these aryl nitromethane precursors. The method efficiently provides a variety of substituted, isolable diaryl nitromethanes. In addition, it is possible to sequentially append two different aryl groups to nitrometha...

Palladium-catalyzed ring-opening thiocarbonylation of vinylcyclopropanes with thiols and carbon monoxide.

Palladium-catalyzed ring-opening thiocarbonylation of vinylcyclopropanes (VCPs) with thiols and carbon monoxide affords the corresponding unsaturated thioesters in moderate to excellent yields. This reaction provides a general method for the ring-opening thiocarbonylation of VCPs. It further demonstrates the utility of transition metal catalysts for the synthesis of organosulfur compounds.