One-pot multicomponent coupling reactions provide a facile synthetic method for creating complex organic molecules starting from readily available reactants without isolation of intermediates. Transition metal catalyzed coupling reactions via C-N bond cleavage is a versatile protocol for synthesizing complex organic products. One of the major challenges has been to overcome lower efficiency in coupling reactions of aliphatic amines. Cleavage of C-N bond of tertiary amines also remains comparatively underdeveloped subfield. Combining C-N bond cleavage with multicomponent reactions would offer an efficient synthetic strategy for forming products without generation of wasteful byproducts and product loss in intermediate steps. Recently, our group developed a three-component deaminative coupling using Ru tetrameric complex with benzoquinone ligand. The reaction afforded coupling of phenols, 2- hydroxybenzaldehyde derivatives and enamines to afford bicyclic 1,3-dioxicin and bicyclic 1,5-dioxicin derivatives. Herein, we report a deaminative three-component coupling reaction of aniline, benzaldehyde, and tertiary amine. The reaction was found to occur via initial formation of imine. Hammett study showed that the there is no significant electronic effect from using benzaldehydes with both electron-withdrawing and donating substituents. Carbon kinetic isotope effect study showed that the rate-determining step is the carbon-nitrogen bond cleavage.

Ruthenium catalyzed carbon-carbon coupling reactions via carbon-nitrogen bond activation for the synthesis of quinoline derivatives

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ACS Fall 2022

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