Gold Catalyzed Synthesis of Substituted Furan by Intermolecular Cascade Reaction of Propargyl Alcohol and Alkyne

Using a combination of triazole-gold (TA-Au) and copper catalysts, the substituted furan was achieved in one pot through a three-step reaction cascade. The reaction tolerates a large substrate scope with simple starting materials. The desired di-, tri-, and tetrasubstituted furans were prepared in good to excellent yields

Palladium-Catalyzed Aminomethylamination and Aromatization of Aminoalkenes with Aminals via C–N Bond Activation

Thanks to the facile imine-enamine tautomerization, the β,γ-unsaturated hydrazones have been successfully utilized as surrogates of aminodienes for realizing the Pd-catalyzed tandem aminomethylamination/aromatization reaction with aminals via C–N bond activation. This direct and operationally simple protocol provides a fundamentally novel strategy to synthesize aromatic heterocycles from alkenes in the absence of external oxidant and base. Mechanistic studies suggested that aminal not only functioned as an aminomethyl source but also acted as formal oxidant and inner base to promote the aromatization

Palladium-Catalyzed Aminomethylamination and Aromatization of Aminoalkenes with Aminals via C–N Bond Activation

Thanks to the facile imine-enamine tautomerization, the β,γ-unsaturated hydrazones have been successfully utilized as surrogates of aminodienes for realizing the Pd-catalyzed tandem aminomethylamination/aromatization reaction with aminals via C–N bond activation. This direct and operationally simple protocol provides a fundamentally novel strategy to synthesize aromatic heterocycles from alkenes in the absence of external oxidant and base. Mechanistic studies suggested that aminal not only functioned as an aminomethyl source but also acted as formal oxidant and inner base to promote the aromatization

Ambient Benzotriazole Ring Opening through Intermolecular Radical Addition to Vinyltriazole

Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode

Ambient Intermolecular [2 + 2] Cycloaddition: An Example of Carbophilicity and Oxophilicity Competition in Au/Ag Catalysis

The gold-catalyzed intermolecular [2 + 2] cycloaddition of propargyl esters was achieved with good stereoselectivity. The “silver-free” condition was critical for this transformation, while only a trace amount of [2 + 2] products were formed in the presence of silver under otherwise identical conditions

Ceric Ammonium Nitrate (CAN) Catalyzed Modification of Ketones <i>via</i> Two C–C Bond Cleavages with the Retention of the Oxo-Group

A simple ceric ammonium nitrate (CAN) catalyzed functionalization of ketones through double C–C bond cleavage strategy has been disclosed. This reaction provides a mild, practical method toward carbamoyl azides, which are versatile intermediates and building blocks in organic synthesis. Based on relevant mechanistic studies, a unique and plausible C–C bond and N–O bond cleavage process is proposed, where the oxyamination intermediate plays an important role in this reaction