ABSTRACT
A straightforward strategy for direct benzylic C-H bond amination via an electrochemical Ritter-type reaction is developed. The reaction demonstrates simpler and milder reaction conditions over the existing methods without extra mediator. Moderate to excellent yields up to 94% of the desired amide products were obtained with a broad substrate scope. The removal of the Ac group by a simple step can afford NH-free benzylic amines, providing a suitable approach for the late-stage functionalization of bioactive molecules.
Subject(s)
Amides , Amines , Amination , Catalysis , Amines/chemistry , Oxidative StressABSTRACT
An Fe(iii)-catalysed transformation of secondary N-phenyl substituted amides to primary amides by an electrochemical method is developed. Regioselective aryl C-H oxygenation occurs during the reaction, promoting selective C(phenyl)-N bond cleavage to form primary amides in yields of up to 92%.
ABSTRACT
A rhodium-catalyzed Suzuki-Miyaura coupling reaction via C(O)-C bond activation to form 2-benzoylpyridine N-oxide derivatives is reported. Both the C(O)-C(sp2) and C(O)-C(sp3) bond could be activated during the reaction with yields up to 92%. The N-oxide moiety could be employed as a traceless directing group, leading to free pyridine ketones.
ABSTRACT
A versatile rhodium-catalyzed/copper-mediated C-H/C-C activation and cascade annulation reaction was described to form 2-arylindole derivatives. Highly selective C-C bond cleavage of γ-substituted tert-propargyl alcohols occurred, together with pyridine-directed ortho C(sp2)-H bond activation, affording a series of 2-arylindoles with yields up to 90%. Subsequent derivations were smoothly conducted to access polyfunctionalized 2-arylindoles, illustrating the potential applications of this method.
